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
收藏
页码：654 / 671
页数：18
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