Total Synthesis of Leucosceptroids A and B

被引：36

作者：

Guo, Sheng ^{[1
]}

Liu, Jie ^{[1
]}

Ma, Dawei ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 04期

基金：

中国国家自然科学基金;

关键词：

aldol reaction; cyclization; natural products; sesterterpenoids; total synthesis; DEFENSIVE SESTERTERPENOIDS; GLANDULAR TRICHOMES; CANUM; CYCLIZATION; HYDROSILYLATION; TERPENOIDS; INDUCTION; ALCOHOLS; KETONES; ACCESS;

D O I：

10.1002/anie.201410134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

LeucosceptroidsA and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram-scale total synthesis of leucosceptroidB and the first total synthesis of leucosceptroidA are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)-citronellal-derived aldehyde, a SmI2-mediated intramolecular ketyl-olefin radical cyclization, and final-stage alcohol oxidation.

引用

页码：1298 / 1301

页数：4

共 33 条

[1]

[Anonymous], 2003, ANGEW CHEM

[2] Enantioselective Intramolecular Aldehyde α-Alkylation with Simple Olefins: Direct Access to Homo-Ene Products [J].

Comito, Robert J. ;

Finelli, Femanda G. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) :9358-9361

[3] PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].

COREY, EJ ;

ENSLEY, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909

[4] A general and efficient synthesis of substituted furans and dihydrofurans via gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols [J].

Du, Xiangwei ;

Song, Feijie ;

Lu, Yuhua ;

Chen, Haoyi ;

Liu, Yuanhong .

TETRAHEDRON, 2009, 65 (09) :1839-1845

[5] 1,5-asymmetric induction in boron-mediated β-alkoxy methyl ketone aldol addition reactions [J].

Evans, DA ;

Côté, B ;

Coleman, PJ ;

Connell, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10893-10898

[6] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

[7] Stability relationships in bicyclic ketones [J].

Gordon, HL ;

Freeman, S ;

Hudlicky, T .

SYNLETT, 2005, (19) :2911-2914

[8]

Huang X., 2013, ANGEW CHEM INT EDIT, V125, P986

[9] Asymmetric Total Synthesis of Leucosceptroid B [J].

Huang, Xuan ;

Song, Liqiang ;

Xu, Jiao ;

Zhu, Guili ;

Liu, Bo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (03) :952-955

[10]

Hugelshofer C.L., 2014, ANGEW CHEM, V126, P11533

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