白海绵内酯A中碳-碳键和碳-碳部分的合成方法。
Approach to the Synthesis of the C-C and C-C portion of Leucascandrolide A.
作者信息
Hunter T J, Zheng J, O'Doherty G A
机构信息
MilliporeSigma, 645 Science Drive, Madison, Wisconsin 53711, United States.
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, United States.
出版信息
Org Chem Front. 2016 Sep 1;3(9):1120-1125. doi: 10.1039/C6QO00284F. Epub 2016 Jul 12.
Abstract
An asymmetric synthesis of the 1 to 11 and 14 to 18 fragments of the macrocyclic portion of the antibiotic Leucascandrolide A was achieved in 21 total steps from an achiral dienoate. The key 4-hydroxy-2,5-pyran portion of the natural product was established by oxy-Michael cyclization of a 5,7,9,11-tetraol intermediate, which in turn was established by an iterative asymmetric-hydration of dienoates. Alternative strategies for establishing the polyol stereochemistry were explored.
摘要
从一种非手性二烯酸酯出发，经21步总反应实现了抗生素白念珠菌素A大环部分1至11片段和14至18片段的不对称合成。天然产物关键的4-羟基-2,5-吡喃部分通过5,7,9,11-四醇中间体的氧-迈克尔环化反应构建而成，而该中间体又通过二烯酸酯的迭代不对称水合反应构建。还探索了构建多元醇立体化学的替代策略。
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