TOTAL SYNTHESIS OF THE ANTIFUNGAL CYCLIC DEPSIPEPTIDES SCH-57697 AND AUREOBASIDIN-A

Authors
JAO E COOPER AB RANE DF SAKSENA AK DESAI J WANG J GIRIJAVALLABHAN VM GANGULY AK
Citation
E. Jao et al., TOTAL SYNTHESIS OF THE ANTIFUNGAL CYCLIC DEPSIPEPTIDES SCH-57697 AND AUREOBASIDIN-A, Tetrahedron letters, 37(32), 1996, pp. 5661-5664
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5661 - 5664
Database
ISI
SICI code
0040-4039(1996)37:32<5661:TSOTAC>2.0.ZU;2-9
Abstract
A novel cyclic depsinonapeptide antifungal 1a (Sch 57697) and its isom er 1b were synthesized by a fragment coupling approach and this method ology was applied to the total synthesis of the natural product aureob asidin A. Synthetic strategies for coupling of N-methyl amino acids wi th minimal racemization are discussed. Biological evaluation of isomer s la and Ib demonstrated the importance of chirality at the beta-hydro xy-N-methylvaline (OHMeVal) position. Copyright (C) 1996 Elsevier Scie nce Ltd