共 26 条
Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Toxicodenane A
被引:3
作者:

Qin, Xu-Long
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h-index: 0
机构:
Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China
Univ Sci & Technol China, Hefei 230026, Anhui, Peoples R China Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China

Wu, Guo-Jie
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h-index: 0
机构:
Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China

Han, Fu-She
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China
Univ Sci & Technol China, Hefei 230026, Anhui, Peoples R China Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China
机构:
[1] Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Synthet Rubber, Jilin 130022, Jilin, Peoples R China
[2] Univ Sci & Technol China, Hefei 230026, Anhui, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
基金:
中国国家自然科学基金;
关键词:
MEDIUM-SIZED CARBOCYCLES;
CONSTRUCTION;
COMBINATION;
D O I:
10.1021/acs.orglett.1c03293
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
We present the first enantioselective total synthesis and absolute configuration assignment of (+)-toxicodenane A via a nine-step sequence from the readily available material. The synthesis features a desymmetric enantioselective reduction of 2,2-disubstituted 1,3-cyclohexanedione for the synthesis of a chiral 2,2-disubstituted 3-hydroxy cyclohexanone building block, a highly diastereoselective Grignard reaction for the incorporation of an allyl group, and a Lewis acid-mediated intramolecular transacetalation and Prins cascade reaction for the construction of oxa-bridged bicyclic rings.
引用
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页码:8570 / 8574
页数:5
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共 26 条
[1]
Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C=N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models
[J].
Bartolo, Nicole D.
;
Read, Jacquelyne A.
;
Valentin, Elizabeth M.
;
Woerpel, K. A.
.
CHEMICAL REVIEWS,
2020, 120 (03)
:1513-1619

Bartolo, Nicole D.
论文数: 0 引用数: 0
h-index: 0
机构:
NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA

Read, Jacquelyne A.
论文数: 0 引用数: 0
h-index: 0
机构:
NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA
Univ Utah, Dept Chem, 315 South 1400 East, Salt Lake City, UT 84112 USA NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA

Valentin, Elizabeth M.
论文数: 0 引用数: 0
h-index: 0
机构:
NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA
Susquehanna Univ, Dept Chem, 514 Univ Ave, Selinsgrove, PA 17870 USA NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA

Woerpel, K. A.
论文数: 0 引用数: 0
h-index: 0
机构:
NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA
[2]
Identification of an unexpected 2-oxonia[3,3]sigmatropic rearrangement/aldol pathway in the formation of oxacyclic rings. Total synthesis of (+)-aspergillin PZ
[J].
Canham, Stephen M.
;
Overman, Larry E.
;
Tanis, Paul S.
.
TETRAHEDRON,
2011, 67 (51)
:9837-9843

Canham, Stephen M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

Overman, Larry E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

Tanis, Paul S.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
[3]
A Total Synthesis of (-)-Hamigeran B and (-)-4-Bromohamigeran B
[J].
Cao, Bao-Chen
;
Wu, Guo-Jie
;
Yu, Fang
;
He, Yu-Peng
;
Han, Fu-She
.
ORGANIC LETTERS,
2018, 20 (12)
:3687-3690

Cao, Bao-Chen
论文数: 0 引用数: 0
h-index: 0
机构:
Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China
Chinese Acad Sci, Changchun Inst Appl Chem, Jilin Prov Key Lab Green Chem & Proc, 5625 Renmin St, Changchun 130022, Jilin, Peoples R China Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China

Wu, Guo-Jie
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Changchun Inst Appl Chem, Jilin Prov Key Lab Green Chem & Proc, 5625 Renmin St, Changchun 130022, Jilin, Peoples R China
State Ocean Adm, Engn Res Ctr Marine Bioresources Comprehens Utili, Xiamen 361005, Fujian, Peoples R China Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China

Yu, Fang
论文数: 0 引用数: 0
h-index: 0
机构:
Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China

He, Yu-Peng
论文数: 0 引用数: 0
h-index: 0
机构:
Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China

Han, Fu-She
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Changchun Inst Appl Chem, Jilin Prov Key Lab Green Chem & Proc, 5625 Renmin St, Changchun 130022, Jilin, Peoples R China Liaoning Shihua Univ, Coll Chem Chem Engn & Environm Engn, Dandong Rd West 1, Fushun 113001, Liaoning, Peoples R China
[4]
Efforts toward the total synthesis of (±)-toxicodenane A utilizing an oxidopyrylium-based [5+2] cycloaddition of a silicon-tethered BOC-pyranone
[J].
Grabowski, Jacob P.
;
Ferrence, Gregory M.
;
Mitchell, T. Andrew
.
TETRAHEDRON LETTERS,
2020, 61 (38)

Grabowski, Jacob P.
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA

Ferrence, Gregory M.
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA

Mitchell, T. Andrew
论文数: 0 引用数: 0
h-index: 0
机构:
Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA
[5]
Two New Sesquiterpenes from the Resin of Toxicodendron vernicifluum
[J].
He, Jiang-Bo
;
Lu, Qing
;
Cheng, Yong-Xian
.
HELVETICA CHIMICA ACTA,
2015, 98 (07)
:1004-1008

He, Jiang-Bo
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
Kunming Univ, Sch Med, Kunming 650214, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China

Lu, Qing
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China

Cheng, Yong-Xian
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
[6]
Sesquiterpenoids with New Carbon Skeletons from the Resin of Toxicodendron vernicifluum as New Types of Extracellular Matrix Inhibitors
[J].
He, Jiang-Bo
;
Luo, Jie
;
Zhang, Li
;
Yan, Yong-Min
;
Cheng, Yong-Xian
.
ORGANIC LETTERS,
2013, 15 (14)
:3602-3605

He, Jiang-Bo
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

Luo, Jie
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

Zhang, Li
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Med Sci, Inst Mat Med, Beijing 100050, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

Yan, Yong-Min
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

Cheng, Yong-Xian
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
[7]
SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS
[J].
HOVEYDA, AH
;
EVANS, DA
;
FU, GC
.
CHEMICAL REVIEWS,
1993, 93 (04)
:1307-1370

HOVEYDA, AH
论文数: 0 引用数: 0
h-index: 0
机构:
HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA

EVANS, DA
论文数: 0 引用数: 0
h-index: 0
机构:
HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA

FU, GC
论文数: 0 引用数: 0
h-index: 0
机构:
HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA
[8]
Diastereoselective Total Synthesis of (±)-Toxicodenane A
[J].
Kobayashi, Toyoharu
;
Yamanoue, Kotono
;
Abe, Hideki
;
Ito, Hisanaka
.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2017, 2017 (45)
:6693-6699

Kobayashi, Toyoharu
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan

Yamanoue, Kotono
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan

Abe, Hideki
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan

Ito, Hisanaka
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan Tokyo Univ Pharm & Life Sci, Sch Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan
[9]
Total Syntheses of Aflavazole and 14-Hydroxyaflavinine
[J].
Li, Hailong
;
Chen, Qifeng
;
Lu, Zhaohong
;
Li, Ang
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2016, 138 (48)
:15555-15558

Li, Hailong
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

Chen, Qifeng
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

Lu, Zhaohong
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

Li, Ang
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[10]
Practical asymmetric approach to medium-sized carbocycles based on the combination of two Ru-catalyzed transformations and a lewis acid-induced cyclization
[J].
López, F
;
Castedo, L
;
Mascareñas, JL
.
ORGANIC LETTERS,
2005, 7 (02)
:287-290

López, F
论文数: 0 引用数: 0
h-index: 0
机构: Univ Santiago, Dept Quim Organ, Santiago De Compostela 15782, Spain

Castedo, L
论文数: 0 引用数: 0
h-index: 0
机构: Univ Santiago, Dept Quim Organ, Santiago De Compostela 15782, Spain

Mascareñas, JL
论文数: 0 引用数: 0
h-index: 0
机构: Univ Santiago, Dept Quim Organ, Santiago De Compostela 15782, Spain