Facile and efficient synthesis of 3β-hydroxy-eupholanost-8-en-24-one.docVIP

Molecules 2001, 6, 468-471 molecules ISSN 1420-3049 Facile and efficient synthesis of 3β-hydroxy-eupholanost-8-en- 24-one N. El Aouad 1,*, A. Benharref 1 and R. Gree 2 1 Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Université Cadi Ayyad, Faculté des Sciences Semlalia. BP 2390 Boulevard Prince My Abdellah. Marrakech, Morocco. Tel: 21244434649; Fax 21244437408; E-mail: noureddine@ucam.ac.ma, benharref@ 2 Laboratoire de Chimie de Synthèse et Activations de Biomolécules, Ecole Nationale Supérieure de Chimie de Rennes. Avenue du Général Leclerc 35700 RENNES, France. *Author to whom correspondence should be addressed; E-mail: noureddine@ucam.ac.ma Received: 24 November 2000; in revised form 20 December 2000 / Accepted: 20 December 2000/ Published: 30 April 2001 Abstract: The epoxidation of the natural product α-euphol followed by cleavage of the obtained epoxide with BF3-etherate, provides 3β-hydroxy-eupholanost-8-en-24-one in satisfactory overall yield. Keywords: α-euphol, 3β-hydroxy-eupholanost-8-en-24-one, epoxide cleavage. Introduction Epoxides are among the most frequently occurring functional groups found in natural products and their synthetic analogues. They have been widely used because of their chemical reactivity [1,2], which can be explained by the ring strain of the small heterocycle. Conversion of epoxides to carbonyl compounds is a synthetically useful reaction, which is commonly achieved by BF3 and its etherate [3]. The present work discloses the application of this methodology to the synthesis of the C24 derivative of α-euphol, a reagent and intermediate in sterol biosynthesis.  Molecules 2001, 6 469 Results and discussion The tetracyclic triterpenes of the euphane class are distinguished from lanostane by C13, C14 and C17 stereochemical inversion. To our knowledge, the literature contains no report of a successful synthetic route to the C24 derivatives of α-eupho