MICROBIAL METABOLITES .11. TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (S)-CARLOSIC ACID (4-BUTYRYL-2,5-DIHYDRO-3-HYDROXY-5-OXO-FURAN-2-ACETIC ACID) AND CONVERSION OF (R)-5-METHYLTETRONIC ACID INTO (R)-CAROLIC ACID (3,4-DIHYDRO-8-METHYLFURO[3,4-B]OXEPIN-5,6(2H,8H)-DI-ONE)

被引：39

作者：

BLOOMER, JL ^{[1
]}

KAPPLER, FE ^{[1
]}

机构：

[1] TEMPLE UNIV, DEPT CHEM, PHILADELPHIA, PA 19122 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1976年 / 14期

关键词：

D O I：

10.1039/p19760001485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of (S)-2,5-dihydro-3-hydroxy-5-oxofuran-2-acetic acid and its methyl ester were described. Biomimetic acylations of the ester and of (R)-3-hydroxy-2-methylfuran-2(5H)-one[R)-.gamma.-methyltetronic acid] to produce (S)-carlosic acid and (R)-carolic acid, respectively, are described. The absolute configuration of carlosic acid from Penicillium charlesii NRRL 1887 was established as S.

引用

页码：1485 / 1491

页数：7

共 44 条

[1] NATURALLY OCCURRING LACTONES AND LACTAMES .4. FRIEDEL-CRAFTS ACYLATION OF TETRONIC ACID NUCLEUS AND SYNTHESIS OF (S)-CAROLIC ACID [J].