Highly efficient, enantioselective synthesis of (+)-grandisol from a C-2-symmetric bis(alpha,beta-butenolide)

Authors
de March, P Figueredo, F Font, J Raya, J
Citation
P. De March et al., Highly efficient, enantioselective synthesis of (+)-grandisol from a C-2-symmetric bis(alpha,beta-butenolide), ORG LETT, 2(2), 2000, pp. 163-165
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
2
Year of publication
2000
Pages
163 - 165
Database
ISI
SICI code
1523-7060(20000127)2:2<163:HEESO(>2.0.ZU;2-Z
Abstract
[GRAPHICS] A new, very efficient, enantioselective synthesis of the sexual attracting insect pheromone (+)-grandisol has been developed, in which the key step is the double [2 + 2] photocycloaddition of ethylene to a bis(alpha,beta-bute nolide) readily available from D-mannitol. The C-2 symmetry of the substrat e and the appropriate protection of the central diol unit are the crucial f eatures for the high diastereofacial discrimination during the cycloadditio n process.