THE FIRST TOTAL SYNTHESIS OF (+)-BULLATACIN, A POTENT ANITITUMOR ANNONACEOUS ACETOGENIN, AND (+)-(15,24)-BISEPI-BULLATACIN

被引：95

作者：

NAITO, H ^{[1
]}

KAWAHARA, E ^{[1
]}

MARUTA, K ^{[1
]}

MAEDA, M ^{[1
]}

SASAKI, S ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,HIGASHI KU,FUKUOKA 812,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 14期

关键词：

D O I：

10.1021/jo00119a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reports the first total synthesis of the natural product (+)-bullatacin (1), a representative of potent antitumor Annonaceous acetogenins, as well as a stereoisomer (+)-(15,24)-bisepi-bullatacin (2). In this synthesis, a new, efficient method has been developed to introduce the gamma-lactone into the bistetrahydrofuran skeleton through in situ alkylation of epoxide 4 by the alpha-sulfonyl carbanion of phenyl sulfone 5. The methylated gamma-lactone was successfully synthesized by a sequence of reactions comprising an aldol reaction, an acidic lactonization, and elimination under mild, basic condition.

引用

页码：4419 / 4427

页数：9

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