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Enantioselective Total Synthesis of (+)‐Hagen's Gland Lactones
Author(s) -
Gharpure Santosh J.,
Nanda Laxmi Narayan,
Shukla Manoj Kumar
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101328
Subject(s) - enantioselective synthesis , chemistry , cyclopropanation , intramolecular force , total synthesis , aldehyde , lactone , diol , organocatalysis , organic chemistry , stereochemistry , ring (chemistry) , catalysis
Enantioselective synthesis of Hagen's gland lactone is described. The enantiomerically enriched diol was prepared by organocatalytic α‐oxidation of the aldehyde. The other key reactions involved a highly diastereoselective intramolecular cyclopropanation of vinylogous carbonates to furnish donor–acceptor‐substituted cyclopropanes and their ring opening and iodolactonization followed by reduction.