A short formal synthesis of squalamine from a microbial metabolite

Authors
Kinney, WA Zhang, XH Williams, JI Johnston, S Michalak, RS Deshpande, M Dostal, L Rosazza, JPN
Citation
Wa. Kinney et al., A short formal synthesis of squalamine from a microbial metabolite, ORG LETT, 2(19), 2000, pp. 2921-2922
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
19
Year of publication
2000
Pages
2921 - 2922
Database
ISI
SICI code
1523-7060(20000921)2:19<2921:ASFSOS>2.0.ZU;2-U
Abstract
[GRAPHICS] A short formal synthesis of squalamine is described, utilizing the biotrans formation product 2, which is available in one step from commercially avail able 3-keto-23,24-bisnorchol-4-en-22-ol (1), Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11 .