An Alkyne Strategy for the Asymmetric Synthesis of Natural Products: Application to (+)‐Spirolaxine Methyl Ether

Abstract

Alkyne of magic: An efficient synthesis of (+)-spirolaxine methyl ether (1) was accomplished by using alkynes as versatile synthetic building blocks. Highlights include two ProPhenol-catalyzed asymmetric alkynylations and a Pd-catalyzed spiroketalization (see scheme; TBS=tert-butyldiphenylsilyl). The use of alkynes alleviates the chemoselectivity issues of ketones and should be widely applicable to natural product synthesis. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z702637_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.