Synthetic applications of the thermal rearrangement of ozonides: First enantiospecific synthesis of marine metabolite Luffarin W

Citation
Af. Barrero et al., Synthetic applications of the thermal rearrangement of ozonides: First enantiospecific synthesis of marine metabolite Luffarin W, SYNLETT, (9), 2000, pp. 1269-1272
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
9
Year of publication
2000
Pages
1269 - 1272
Database
ISI
SICI code
0936-5214(200009):9<1269:SAOTTR>2.0.ZU;2-W
Abstract
The ozonides on quaternary carbons undergo thermal rearrangement to yield a mixture of formates and alkenes. This reaction constitutes an alternative procedure to the unusual Baeyer-Villiger rearrangement of aliphatic aldehyd es. The first enantiospecific synthesis of the marine metabolite Luffarin W from (-)-sclareol has been carried out, based on this methodology.