American Chemical Society
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Enantioselective Synthesis of a Mitosane Core Assisted by Diversity-Based Catalyst Discovery

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journal contribution
posted on 2001-08-03, 00:00 authored by Nikolaos Papaioannou, Catherine A. Evans, Jarred T. Blank, Scott J. Miller
Synthesis of mitosane 1 in optically pure form is reported. A retrosynthetic plan that proceeds through racemic allylic alcohol 3 was carried out. This intermediate served as a test substrate for a rapid screen of a small library (152 members) of peptide-based kinetic resolution catalysts. Peptide 9 was found to effect kinetic resolution with krel = 27. Alcohol (−)-3 was then converted to optically pure (−)-1 in eight steps.