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 | Zendy

Özlügedik Mustafa | Zendy; Ünaldi Seda | Zendy; Wibbeling Birgit | Zendy; Hoppe Dieter | Zendy

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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.

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