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Synfacts 2008(3): 0231-0231  
DOI: 10.1055/s-2008-1042652
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Spirolaxine Methyl Ether

Contributor(s):Philip Kocienski, Stewart Eccles
B. M. Trost*, A. H. Weiss
Stanford University, USA
An Alkyne Strategy for the Asymmetric Synthesis of Natural Products: Application to (+)-Spirolaxine Methyl Ether
Angew. Chem. Int. Ed.  2007,  46, 7664-7666  
Further Information

Publication History

Publication Date:
21 February 2008 (online)

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Key words

asymmetric alkynylation - spiroacetalization - palladium

Significance

The spirolaxine family was isolated from Sporotichum laxum and has shown several different biological activities including potent activity against Helicobacter pylori. This synthesis of spirolaxine methyl ether features an efficient asymmetric alkynylation (A→D) catalyzed by the phenol C.

Comment

Nearly the entire framework of spirolaxine was put together using alkyne chemistry. The internal alkyne I was used as an electrophilic ketone surrogate - a strategy pioneered by Utimoto (Pure Appl. Chem. 1983, 55, 1845).

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