Stereoselective Formal Synthesis of (+)-Allokainic Acid via Thiol-Mediated Acyl Radical Cyclization

被引：19

作者：

Yamada, Ken-ichi ^{[1
]}

Sato, Tomohiro ^{[1
]}

Hosoi, Masaki ^{[1
]}

Yamamoto, Yasutomo ^{[2
]}

Tomioka, Kiyoshi ^{[2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 606, Japan

[2] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, Kyoto 6100395, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2010年 / 58卷 / 11期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

(+)-allokainic acid; acyl radical cyclization; thiol; stereoselective synthesis; C-H INSERTION; (+)-ALPHA-ALLOKAINIC ACID; ENANTIOSELECTIVE SYNTHESIS; (-)-ALPHA-KAINIC ACID; CARBOCYCLIZATION; CONSTRUCTION; PYRROLIDINES; KAINOIDS; BOND;

D O I：

10.1248/cpb.58.1511

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Stereoselective formal synthesis of (+)-allokainic acid was accomplished starting from L-glutamate by using a thiol-mediated acyl radical cyclization as a key step. The cyclization of a formylalkenoate proceeded in a highly diastereoselective manner to give trans-4,5-disubstituted pyrrolidin-3-one without the production of the cis-isomer. The pyrrolidinone was then converted into the established synthetic intermediate of (+)-allokainic acid via the iron-catalyzed coupling reaction with an isopropenyl Grignard reagent.

引用

页码：1511 / 1516

页数：6

共 50 条

[21] Thiol-mediated free radical cyclisations of isocyanides on solid support
Lamberto, M
Corbett, DF
Kilburn, JD
TETRAHEDRON LETTERS, 2004, 45 (46) : 8541 - 8543
[22] STEREOSELECTIVE SYNTHESIS OF CIS-2,5-DISUBSTITUTED TETRAHYDROFURAN-3-ONES VIA AN ACYL RADICAL CYCLIZATION
EVANS, PA
ROSEMAN, JD
TETRAHEDRON LETTERS, 1995, 36 (01) : 31 - 34
[23] SHORT AND EFFICIENT STEREOSELECTIVE SYNTHESIS OF ALPHA-ALLOKAINIC ACID
OPPOLZER, W
ANDRES, H
TETRAHEDRON LETTERS, 1978, (36) : 3397 - 3400
[24] Nitrogen heterocycles via palladium-catalyzed carbocyclization.: Formal synthesis of (+)-α-allokainic acid
Cook, GR
Sun, LD
ORGANIC LETTERS, 2004, 6 (14) : 2481 - 2484
[25] A radical mediated approach to the stereoselective formal total synthesis of (+)-Sch 642305
Chakraborty, Tushar Kanti
Samanta, Rajarshi
Kumar, Pulukuri Kiran
TETRAHEDRON, 2009, 65 (34) : 6925 - 6931
[26] Synthesis of the Core of Actinophyllic Acid Using a Transannular Acyl Radical Cyclization
Zaimoku, Hisaaki
Taniguchi, Tsuyoshi
Ishibashi, Hiroyuki
ORGANIC LETTERS, 2012, 14 (06) : 1656 - 1658
[27] Synthesis of macrocyclic thiolactone peptides via radical acyl thiol-ene
Benny, Alby
Scanlan, Eoin
JOURNAL OF PEPTIDE SCIENCE, 2024, 30
[28] Chemical Groups and Structural Characterization of Lignin via Thiol-Mediated Demethylation
Hu, Lihong
Pan, Hui
Zhou, Yonghong
Hse, Chung-Yun
Liu, Chengguo
Zhang, Baofang
Xu, Bin
JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, 2014, 34 (02) : 122 - 134
[29] A concise stereoselective formal total synthesis of the cytotoxic macrolide (+)-Neopeltolide via Prins cyclization
Yadav, Jhillu Singh
Kumar, Gunda Gopala Krishana Satya Narayana
TETRAHEDRON, 2010, 66 (02) : 480 - 487
[30] Synthesis of optically active trifluoromethylated indolizidine derivatives via stereoselective radical cyclization
Okano, T
Fumoto, M
Kusukawa, T
Fujita, M
ORGANIC LETTERS, 2002, 4 (09) : 1571 - 1573

← 1 2 3 4 5 →