Affiliation:
1. Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan
Abstract
Naturally occurring carbohydrates serve as useful building blocks, and various derivatives have been employed in natural product syntheses. For instance, some aldoses can be converted to 1,3-dienes via the Wittig reaction at the anomeric carbon, accompanied by the E2 elimination of the C3-alkoxy group. However, there are few examples of terminal 1,3-diene synthesis. We report the synthesis of (S,Z)-1,4-bis(benzyloxy)hexa-3,5-dien-2-ol, featuring a terminal 1,3-diene and chiral secondary alcohol, derived from 2,3,5-tri-O-benzyl-d-arabinofuranose with methyltriphenylphosphonium bromide and potassium tert-butoxide in a single step. The synthesized terminal 1,3-diene demonstrated effective reactivity in a cross-metathesis reaction with cis-1,4-diacetoxy-2-butene.
Reference13 articles.
1. Approaches to the total synthesis of natural products using “chiral templates” derived from carbohydrates;Hanessian;Acc. Chem. Res.,1979
2. Total syntheses of bioactive natural products from carbohydrates;Tatsuta;Sci. Technol. Adv. Mater.,2006
3. Enantiospecific total synthesis of pseudomonic acids from arabinose;Fleet;Tetrahedron Lett.,1983
4. Total synthesis of (2S,3S,5S,10S)-6,9-epoxynonadec-18-ene-7,10-diol and formal total synthesis of (+)-trans-kumausyne from D-arabinose;Gadikota;J. Org. Chem.,2001
5. A total synthesis of macrosphelides C and F from L-(+)-arabinose;Sharma;Tetrahedron Lett.,2003