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Synthesis of Stereoisomers of Cryptofolione 6′‐Mono‐ and 4′,6′‐Di‐ O ‐benzyl Ethers
Author(s) -
Sabitha Gowravaram,
Bhaskar Vangala,
Siva Sankara Reddy S.,
Yadav J. S.
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201190015
Subject(s) - chemistry , propargyl alcohol , iodobenzene , epoxide , wittig reaction , propargyl , ether , alcohol , metathesis , organic chemistry , grignard reaction , ring closing metathesis , stereochemistry , catalysis , polymerization , reagent , polymer
Synthesis of stereoisomers of 6′‐mono‐ and 4′,6′‐di‐ O ‐benzyl cryptofolione is described through a key intermediate 6 , which was prepared by coupling of iodobenzene 8 with chiral propargyl alcohol 9 under Cosford protocol conditions. Monobenzyl ether 4 is obtained via epoxide 6 opening with vinyl Grignard, followed by cross‐metathesis reaction with a vinyl lactone 11 . Whereas, dibenzyl ether 5 is prepared by epoxide 6 opening with chiral propargyl alcohol 7 followed by simple transformations and finally cis ‐Wittig olefination.