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Synthesis of Enantioenriched trans ‐Fused Bicyclo[4.4.0]‐ dec‐3‐enes and Bicyclo[4.3.0]non‐3‐enes Bearing a 1,5‐Lactone Bridge
Author(s) -
Özlügedik Mustafa,
Ünaldi Seda,
Wibbeling Birgit,
Hoppe Dieter
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505143
Subject(s) - chemistry , lactone , enantioselective synthesis , bicyclic molecule , stereochemistry , olefin fiber , acrolein , organic chemistry , catalysis
The combination of (−)‐sparteine‐mediated lithiation of (2‐methyl‐cyclohex‐1‐enyl)methyl or (2‐butyl‐cyclopent‐1‐enyl)methyl carbamate and enantioselective homoaldol reaction with acrolein, transformation to a γ‐lactone, enolate allylation, followed by a ring‐closing olefin metathesis provides a facile entry to tricyclic lactones of type 7 , bearing a 1,5‐lactone bridge.