Function-Oriented Synthesis: Studies Aimed at the Synthesis and Mode of Action of 1-Alkyldaphnane Analogues

Org. Lett., 9 (9), 1829 -1832, 2007. 10.1021/ol0705649 S1523-7060(07)00564-0
Web Release Date: April 5, 2007

Function-Oriented Synthesis: Studies Aimed at the Synthesis and Mode of Action of 1-Alkyldaphnane Analogues

Paul A. Wender,* Noel D'Angelo, Vassil I. Elitzin, Martin Ernst, Eileen E. Jackson-Ugueto, John A. Kowalski, Sharon McKendry, Markus Rehfeuter, Robert Sun, and David Voigtlaender

Department of Chemistry and Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080

wenderp@stanford.edu

Received March 6, 2007

Abstract:

An efficient synthetic route to the ABC tricyclic core of 1

-alkyldaphnanes has been developed. The conformational bias imparted by the C6-C9 oxo-bridge of BC-ring system 12 was used to elaborate the ABC-ring system precursor including the introduction of the

-C5 hydroxyl group. A completely diastereoselective palladium-catalyzed enyne cyclization was then employed to establish the A-ring with a C1 appendage.

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