Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

被引：8

作者：

Ota, Koichiro ^{[1
]}

Kurokawa, Takao ^{[1
]}

Kawashima, Etsuko ^{[1
]}

Miyaoka, Hiroaki ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

来源：

MARINE DRUGS | 2009年 / 7卷 / 04期

关键词：

xestenone; marine norditerpene; total synthesis; structural determination; SPONGE XESTOSPONGIA-VANILLA; KETONES;

D O I：

10.3390/md7040654

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis.

引用

页码：654 / 671

页数：18

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