Two Concise Total Syntheses of (-)-Bitungolide F

被引：18

作者：

ElMarrouni, Abdelatif ^{[1
]}

Joolakanti, Shyamsunder R. ^{[1
]}

Colon, Aude ^{[1
]}

Heras, Montserrat ^{[1
]}

Arseniyadis, Stellios ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, Chim Organ Lab, CNRS, F-75231 Paris 05, France

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 18期

关键词：

ANTIFUNGAL ANTIBIOTICS PHOSLACTOMYCINS; COLONY-STIMULATING FACTORS; ASYMMETRIC TOTAL-SYNTHESIS; FAMILY INDUCE PRODUCTION; OLEFIN CROSS-METATHESIS; MARROW STROMAL CELLS; MICROBIAL METABOLITES; LEUSTRODUCSIN-B; ALDOL REACTIONS; DELTA-LACTONES;

D O I：

10.1021/ol101659y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective total synthesis of the dual-specificity phosphatase inhibitor (-)-bitungolide F has been achieved using two convergent routes. Both strategies feature an asymmetric boron-mediated pentenylation, a stereoselective aldol, and a hydroxyl-directed 1,3-anti-reduction in order to control the stereogenic centers at C4, C5, C9, and C11. Whereas the first total synthesis was achieved in 11 steps and 14.6% overall yield using an Evans-type asymmetric alkylation, the second was completed in 9 steps and 11.4% overall yield using a highly enantioselective organocatalytic Michael addition as a key step and a protecting group free strategy,

引用

页码：4074 / 4077

页数：4

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