CONSTRUCTION OF QUATERNARY CARBON CENTERS BY PALLADIUM-CATALYZED INTRAMOLECULAR ALKENE INSERTIONS - TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOIDS (+/-)-TAZETTINE AND (+/-)-6A-EPIPRETAZETTINE

被引：116

作者：

ABELMAN, MM ^{[1
]}

OVERMAN, LE ^{[1
]}

TRAN, VD ^{[1
]}

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 19期

关键词：

D O I：

10.1021/ja00175a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total syntheses of (±)-tazettine (1) and (±)-6a-epipretazettine (3), which proceed in 11 steps from the known enal 7(14 steps from commercially available p-methoxybenzyl alcohol), are reported. The pivotal step is the palladium-catalyzed cyclization of alkenyl aryl iodide 13, which proceeded in excellent yield (63-90%) and with high stereoinduction (>20:1) to form 14. © 1990, American Chemical Society. All rights reserved.

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页码：6959 / 6964

页数：6

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