Total synthesis of VM55599. Utilization of an intramolecular Diels-Alder cycloaddition of potential biogenetic relevance

Authors
Stocking, EM Sanz-Cervera, JF Williams, RM
Citation
Em. Stocking et al., Total synthesis of VM55599. Utilization of an intramolecular Diels-Alder cycloaddition of potential biogenetic relevance, J AM CHEM S, 122(8), 2000, pp. 1675-1683
Citations number
73
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
122
Issue
8
Year of publication
2000
Pages
1675 - 1683
Database
ISI
SICI code
0002-7863(20000301)122:8<1675:TSOVUO>2.0.ZU;2-X
Abstract
The total synthesis of VM55599, a natural metabolite of Penicillium sp. IMI 332995, has been achieved via an intramolecular Diels-Alder cycloaddition o f a reverse isoprene moiety across an azadiene system. The diastereoselecti vity of the intramolecular Diels-Alder cycloaddition has biogenetic implica tions and is discussed in the context of the biogenetic relationship of VM5 5599 to the paraherquamides.