Short and efficient route to the fully functionalized polar core of scyphostatin
Emmanuel N Pitsinos1, Ana Cruz
1Laboratory of Natural Products Synthesis and Bioorganic Chemistry, Institute of Physical Chemistry, NCSR Demokritos, P.O. Box 60228, GR-153 10 Aghia Paraskevi, Athens, Greece. pitsinos@chem.demokritos.gr
Abstract:
[reaction: see text]. Diastereoselective oxidative dearomatization of benzopyran 5 to the corresponding p-quinol 9b allows a fast, efficient, and versatile entry to scyphostatin's polar epoxycyclohexenone moiety as demonstrated by the preparation of its palmitoyl analogue 16 (R = (CH2)14CH3).
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