TOTAL SYNTHESIS OF THE LATRUNCULINS

被引：46

作者：

SMITH, AB ^{[1
]}

LEAHY, JW ^{[1
]}

NODA, I ^{[1
]}

REMISZEWSKI, SW ^{[1
]}

LIVERTON, NJ ^{[1
]}

ZIBUCK, R ^{[1
]}

机构：

[1] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 08期

关键词：

D O I：

10.1021/ja00034a036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total syntheses of (+)-latrunculin A (1) and (+)-latrunculin B (2), two architecturally novel toxins isolated from the Red Sea sponge Latrunculia magnifica (Keller), have been achieved via highly convergent and stereocontrolled routes (longest linear sequences, 16 and 12 steps, respectively). Formal syntheses of scalemic latrunculins C (3) and M (5) also derive from the construction of 2. Central features of the unified synthetic strategy include the aldol reaction of aldehyde (-)-12 with methyl ketone (-)-13, a novel acid-catalyzed reorganization-equilibration of ortho ester (-)-11, and Mitsunobu macrolide cyclization.

引用

页码：2995 / 3007

页数：13

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