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Iodine‐Catalyzed Highly Diastereoselective Synthesis of trans ‐2,6‐Disubstituted‐3,4‐Dihydropyrans: Application to Concise Construction of C28–C37 Bicyclic Core of (+)‐Sorangicin A
Author(s) -
Mohapatra Debendra K.,
Das Pragna P.,
Pattanayak Manas Ranjan,
Yadav J. S.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902999
Subject(s) - octane , yield (engineering) , silane , iodine , catalysis , bicyclic molecule , ring (chemistry) , combinatorial chemistry , chemistry , organic chemistry , materials science , composite material
A novel iodine‐catalyzed highly diastereoselective synthesis of trans ‐2,6‐disubstituted‐3,4‐dihydropyrans have been achieved from δ‐hydroxy α,β‐unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28–C37 dioxabicyclo[3.2.1]octane ring system of (+)‐sorangicin A in 8 steps with 21 % overall yield.