Asymmetric Total Synthesis of Inthomycins A, B, and C

被引：8

作者：

Kim, Jae Hyun ^{[1
]}

Song, Yeonghun ^{[1
]}

Kim, Min Jung ^{[1
]}

Kim, Sanghee ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Seoul 08826, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

STEREOSPECIFIC SYNTHESIS; ABSOLUTE-CONFIGURATION; CELLULOSE BIOSYNTHESIS; SELECTIVE REDUCTIONS; CHIRAL SYNTHESIS; OXAZOLOMYCIN; PHTHOXAZOLIN; 16-METHYLOXAZOLOMYCIN; ORGANOBORANES; REINSTATEMENT;

D O I：

10.1021/acs.joc.0c00017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the asymmetric total syntheses of inthomycin antibiotics containing a methylene-interrupted oxazolyl-triene motif. Utilizing the alpha,beta-unsaturated aldehyde as a common intermediate, all three inthomycins A-C were divergently synthesized. The asymmetric ynone reduction provided an R-configured secondary alcohol as in the natural products with high enantioselectivity. The geometrically different triene units for each inthomycin were stereoselectively established via methyl cuprate conjugate addition, isomerization of the alpha,beta-unsaturated aldehyde intermediate, and stereoretentive cross-coupling reactions.

引用

页码：4795 / 4806

页数：12

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