Synthesis of (-)-Virginiae Butanolide A (VB-A)

被引：0

作者：

Donges, Jonas ^{[1
]}

Frank, Andrea ^{[1
]}

Schollmeyer, Dieter ^{[1
]}

Nubbemeyer, Udo ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Organ Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 03期

关键词：

bioactive gamma-butyrolactone; diastereoselective synthesis; defined stereotriad; OH-group inversion; oxidation reduction sequence; iodocyclization; ozonolysis; GAMMA-BUTYROLACTONE AUTOREGULATORS; ANTIBIOTIC PRODUCTION; SECONDARY METABOLISM; ANTHRACYCLINE BIOSYNTHESIS; MORPHOLOGICAL DEVELOPMENT; VIRGINIAMYCIN PRODUCTION; STREPTOMYCES-COELICOLOR; ABSOLUTE-CONFIGURATION; ASYMMETRIC-SYNTHESIS; SIGNALING MOLECULES;

D O I：

10.1055/a-2195-7907

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-(1 '-hydroxyalkyl) paraconyl alcohols (-)-VB-A and (-)-SCB-5 are known as highly active signaling molecules within antibiotics production in Streptomyces sp. These gamma-butyrolactone type compounds are epimeric at the 1 '-OH-group. A direct synthesis of (-)-VB-A from (-)-SCB-5 that uses a late-stage inversion of the 1 '-hydroxy group is not favored because of side reactions of the carbinol in beta-position to the lactone C=O function. Therefore, an orthogonally protected 1,4-diol incorporating the central syn/anti 1 ',2,3-stereotriad as described within the (-)-SCB-5 synthesis was used as an advanced intermediate to generate (-)-VB-A, too. A combination of protecting group operations and a 1 '-OH group inversion via oxidation and diastereoselective reduction delivered the anti/anti 1 ',2,3-stereotriad. Final transformations related to that as described for (-)-SCB-5 enabled completion of the (-)-VB-A-synthesis.

引用

页码：445 / 454

页数：10