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Total Synthesis of (+)-alpha-onocerin in Four Steps via Four-Component Coupling and Tetracyclization Steps

Total Synthesis of (+)-alpha-onocerin in Four Steps via Four-Component Coupling and Tetracyclization Steps

Yuan Mi, Jürg V Schreiber, E J Corey

J Am Chem Soc. 2002 Sep 25;124(38):11290-1.

PMID: 12236742

Abstract:

A remarkably short (four steps, 31% overall yield) enantioselective synthesis of the structurally unique C2-symmetric tetracyclic triterpene (+)-alpha-onocerin (1) has been developed. The brevity of this mechanism depends on the assembly of four fragments (two molecules of a chiral epoxy ketone and two molecules of vinyllithium) to generate the chiral bis-epoxide 4 in one step, and on the efficient formation of all four carbocyclic rings in one step by cation-olefin tetracyclization. New and general methodology for the conversion of vinyl tert-butyldimethylsilyl ethers to vinyl triflates with retention of E or Z olefinic geometry also was utilized in the synthesis of 1. A short enantioselective synthesis of a non-C2-symmetric diastereomer of 1 is also described which uses the new methodology.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP511013	Alpha-onocerin		511-01-3	Price

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