A general synthetic route towards gamma- and delta-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide.

摘要

Five (or six) membered asymmetric lactones are synthesized from gamma-butyrolactone (or delta-valerolactone) in a straightforward way using the following reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asymmetric dihydroxylation, oxidation and lactonization. Thus, (-)-muricatacin is synthesized in six steps (43 % overall yield). Furthermore, (5R,6S)-6-acetoxy-hexadecanolide is prepared in eight steps (38 % overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereochemistry. (C) 1999 Elsevier Science Ltd. All rights reserved. [References: 22]