A concise total synthesis of (+/-)-bakkenolide A by means of an intramolecular Diels-Alder reaction

Authors
Back, TG Payne, JE
Citation
Tg. Back et Je. Payne, A concise total synthesis of (+/-)-bakkenolide A by means of an intramolecular Diels-Alder reaction, ORG LETT, 1(4), 1999, pp. 663-665
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
4
Year of publication
1999
Pages
663 - 665
Database
ISI
SICI code
1523-7060(19990826)1:4<663:ACTSO(>2.0.ZU;2-G
Abstract
(+/-)-Bakkenolide A was prepared in five steps from ethyl 4-benzyloxyacetoa cetate by sequential alkylations with tiglyl bromide and cis-5-bromo-1,3-pe ntadiene, followed by an intramolecular Diels-Alder reaction as the key ste p. The known 7-epibakkenolide A and novel 10-epi- and 7,10-diepibakkenolide A stereoisomers were obtained as minor byproducts.