SYNTHETIC STUDIES ON WEDELIGENIN - PREPARATION OF AN A/B-RING INTERMEDIATE

被引：1
|
作者：
MACLEOD, JK
MORRIS, KB
机构：
[1] Research School of Chemistry, Australian National University, Canberra
来源：
AUSTRALIAN JOURNAL OF CHEMISTRY | 1995年 / 48卷 / 03期
关键词：
D O I：
10.1071/CH9950609
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In a new approach to the synthesis of wedeligenin, an A/B-ring intermediate (13a) has been synthesized. The beta-keto ester (15) was readily prepared from Wieland-Meischer ketone in three steps. Baeyer-Villiger oxidation of (15) and subsequent methylenation provided an alkene (16) which contained the malonyl substituent, later to become the gem-diester of (13a). Regiospecific conversion of the alkene into a bromohydrin followed by cyclization afforded (13a). This provided an A/B-ring intermediate which could be further elaborated to allow C/D-ring annulation.
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收藏
页码：609 / 624
页数：16
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