Plakortone B 的全合成。

Total synthesis of plakortone B.

机构信息

Department of Chemistry, Centre of Novel Functional Molecules, Institute of Chinese Medicine and Institute of Molecular Technology for Drug Discovery and Synthesis, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.

出版信息

Chemistry. 2010 Jun 18;16(23):6933-41. doi: 10.1002/chem.201000189.

DOI:10.1002/chem.201000189

PMID:20432418

Abstract

Plakortone B is a naturally occurring bicyclic[3.3.0]furanolactone compound with attractive bioactivities. Although the relative configuration of plakortone B's central core had been established by NMR spectroscopic methods, the absolute configuration of its four stereocenters remained unknown. In the present paper, all four possible isomers of plakortone B were synthesized and one of these molecules was found to be identical with the natural plakortone B on the basis of (1)H, (13)C NMR spectra and specific rotation comparisons. Thus, the absolute configuration of the natural plakortone B was determined to be (3S,4S,6R,10R).

摘要

普拉克托酮 B 是一种天然存在的双环[3.3.0]呋喃内酯化合物，具有吸引人的生物活性。尽管普拉克托酮 B 的中环的相对构型已通过 NMR 光谱方法确定，但四个立体中心的绝对构型仍不清楚。在本文中，合成了普拉克托酮 B 的所有四个可能的异构体，其中一个分子根据（1）H、（13）C NMR 光谱和比旋光度比较，被发现与天然普拉克托酮 B 完全相同。因此，确定天然普拉克托酮 B 的绝对构型为 (3S,4S,6R,10R)。