Total Synthesis of S-(+)-Argentilactone

M uham m ad Saeed3, M uham m ad A bbas3, Khalid M oham m ad K hanb, and Wolfgang V oelter3 a Abteilung für Physikalische Biochemie, Physiologisch-chemisches Institut der Universität Tübingen, Hoppe-Seyler-Straße-4, D-72076 Tübingen, Germany b International Center for Chemical Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi-75276, Pakistan Reprint request to Prof. W. Voelter. E-mail: [email protected] Dedicated to Professor Gerard Descotes, Universite Claude Bernard, Lyon 1, France Z. Naturforsch. 56b, 325-328 (2001); received December 16, 2000 Argentilactone, Carbohydrate Templates, Asymmetrie Total Synthesis Asymmetrie total synthesis of S-(+)-argentilactone (2) was accomplished, using methyl-aD-glucopyranoside (3) as carbohydrate template. Benzylidene acetal 5 was hydrolysed with fBuOOH/AlCl3 and further manipulated to produce the aldehyde 10. A Wittig reaction and subsequent oxidation of the anomeric position yielded the target argentilactone.