Concise Synthesis of (-)-GA18 Methyl Ester

被引：6

作者：

Li, Lei ^{[1
,2
]}

Liang, Weida ^{[2
]}

Rivera, Mario E. ^{[1
,2
]}

Wang, Ye-Cheng ^{[2
]}

Dai, Mingji ^{[1
,2
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

[2] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 145卷 / 01期

关键词：

STEREOSPECIFIC TOTAL-SYNTHESIS; DIELS-ALDER REACTION; GIBBERELLIC-ACID; IMMATURE SEEDS; FURAN-DIENE; STRATEGY; CONSTRUCTION; CHEMISTRY; A15;

D O I：

10.1021/jacs.2c12470

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gibberellins (GAs) are important plant hormones, but some of their family members are in extremely limited natural supply including GA18. Herein, we report a concise synthesis of (-)-GA18 methyl ester, a member of the C20 gibberellins, from commercially available and cheap andrographolide. Our synthesis features an intramolecular ene reaction to form the C ring, an oxidative cleavage followed by aldol condensation to realize a ring contraction and form the challenging trans-hydrindane (AB ring), and a photochemical [2+2] cycloaddition accompanied by a subsequent SmI2-mediated skeletal rearrangement to construct the methylenebicyclo[3.2.1]octanol moiety (CD ring).

引用

页码：53 / 57

页数：5

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