Journal of the American Chemical Society, Vol.117, No.21, 5757-5762, 1995
Highly Diastereoselective Cyclopentane Construction - Enantioselective Synthesis of the Dendrobatid Alkaloid 251F
We report the first total synthesis, and thus structural confirmation, of the dendrobatid alkaloid 251F (1), based on the retrosynthetic analysis illustrated (1 <-- <-- 4). Key observations in this synthesis are that both the Rh-mediated cyclization of 1 and the anionic cyclization of 2 proceed with excellent diastereoselectivity.
Keywords:HOMOGENEOUS ASYMMETRIC HYDROGENATION;PRIMARY ALCOHOLS;DEOXYGENATION;RESOLUTION;EPOXIDATION;CONVERSION;CLEAVAGE;ANALOGS;KETONES;ESTERS