Stereoselective Total Synthesis of Tarchonanthuslactone and Formal Synthesis of (-)-Colletol

Abstract A simple and efficient stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol is described using as the key steps Jacobsen’s kinetic resolution and a Sharpless asymmetric epoxidation. The synthesis of tarchonanthuslactone and the seco acid proceeded in...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2007-12, Vol.2007 (23), p.3639-3646
Main Authors: Yadav, J. S., Reddy, P. Murali, Gupta, Manoj K., Chary, Ch. Janardhana
Format: Article
Language:English
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Summary:Abstract A simple and efficient stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol is described using as the key steps Jacobsen’s kinetic resolution and a Sharpless asymmetric epoxidation. The synthesis of tarchonanthuslactone and the seco acid proceeded in 14% and 13% overall yield, respectively, starting from chiral (R)-propylene oxide.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2007-990850