Function-oriented synthesis: studies aimed at the synthesis and mode of action of 1alpha-alkyldaphnane analogues |
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Authors: | Wender Paul A D'Angelo Noel Elitzin Vassil I Ernst Martin Jackson-Ugueto Eileen E Kowalski John A McKendry Sharon Rehfeuter Markus Sun Robert Voigtlaender David |
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Institution: | Department of Chemistry and Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu |
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Abstract: | reaction: see text] An efficient synthetic route to the ABC tricyclic core of 1alpha-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 beta-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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