Total synthesis of the reputed structure of alcyonin and reassignment of its structure

被引：29

作者：

Corminboeuf, O ^{[1
]}

Overman, LE ^{[1
]}

Pennington, LD ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol034384k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Introduction of the C4 hydroxyl group by an epoxy ester rearrangement is a pivotal step in the first total synthesis of the purported structure of alcyonin. As the spectral data for diol acetate 3 do not match those reported for alcyonin, the structure of this marine diterpene must be revised. Reexamination of NMR spectra, MS data, and chemical transformations of natural alcyonin suggests that the structure of this marine metabolite is allylic peroxide 15.

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页码：1543 / 1546

页数：4

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