Total synthesis of S-(+)-argentilactone

Authors
Saeed, M Abbas, M Khan, KM Voelter, W
Citation
M. Saeed et al., Total synthesis of S-(+)-argentilactone, Z NATURFO B, 56(3), 2001, pp. 325-328
Citations number
19
Categorie Soggetti
Chemistry
Journal title
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
ISSN journal
09320776 → ACNP
Volume
56
Issue
3
Year of publication
2001
Pages
325 - 328
Database
ISI
SICI code
0932-0776(200103)56:3<325:TSOS>2.0.ZU;2-I
Abstract
Asymmetric total synthesis of S-(+)-argentilactone (2) was accomplished, us ing methyl-alpha -D-glucopyranoside (3) as carbohydrate template. Benzylide ne acetal 5 was hydrolysed with (BuOOH)-Bu-1/AlCl3 and further manipulated to produce the aldehyde 10. A Wittig reaction and subsequent oxidation of t he anomeric position yielded the target argentilactone.