C-19 QUASSINOIDS - TOTAL SYNTHESIS OF DL-SAMADERIN-B

被引：23

作者：

GRIECO, PA

PINEIRONUNEZ, MM

机构：

[1] Ernest E. Campaigne and Marvin Carmack Laboratory of Organic Chemistry, Department of Chemistry, Indiana University, Bloomington

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 17期

关键词：

D O I：

10.1021/ja00096a018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of the novel C-19 quassinoid dl-samaderin B (2) is described. The synthesis commences with the known racemic pentacyclic ketone 6, which permits introduction of the C(11), C(12) trans diaxial arrangement of the hydroxyl groups in ring C. The synthesis features a copper(II)-mediated ring contraction of a delta-lactone (28) to a gamma-lactone (29). Subsequent elaboration of the ring A 1 beta-hydroxy-2-oxo-Delta(3,4) olefin unit, cleavage of the C(7), C(11) methoxymethyl ethers, selective oxidation at C(7), and deprotection of the C(1) hydroxyl affords samaderin B (2).

引用

页码：7606 / 7615

页数：10

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