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Published on: October 30, 2018
Synthesis of Strophasterols C, E, and F
Shuntaro Sato1, Shigefumi Kuwahara1
1Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki Aza-Aoba , Aoba-ku, Sendai 980-8572 , Japan.
Abstract:
The synthesis of strophasterols C, E, and F has been accomplished from a 14,15-secoergostane derivative via a 1,3-dipolar cycloaddition of a nitrile oxide intermediate to simultaneously install an isolated cyclopentane ring and a C23 oxygen functionality in a diastereoselective manner and a regio- and diastereoselective selenohydroxylation of an olefinic intermediate under thermodynamic conditions. This synthesis also enabled the stereochemical confirmation of strophasterol C.
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