Stereoselective total syntheses of (+/-)-arthrinone and related natural compounds

Authors
Uchiyama, M Kimura, Y Ohta, A
Citation
M. Uchiyama et al., Stereoselective total syntheses of (+/-)-arthrinone and related natural compounds, TETRAHEDR L, 41(51), 2000, pp. 10013-10017
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
51
Year of publication
2000
Pages
10013 - 10017
Database
ISI
SICI code
0040-4039(200012)41:51<10013:STSO(A>2.0.ZU;2-U
Abstract
The first total syntheses of (+/-)-arthrinone, (+/-)-1-dehydroxyarthrinone, and (+/-)-3a,9a-deoxy-3a-hydroxy-1-dehydroxyarthrinone, antifungal metabol ites from the coprophilous fungus Cercophora sordarioides, were accomplishe d in a stereoselective manner. The ring systems of these metabolites, which were rare among natural products, were efficiently and diastereoselectivei y assembled using the [2,3]Wittig rearrangement and Diels-Alder reaction as the key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.