TY - JOUR AU - Feuillastre, Sophie; Piva, Olivier TI - Total Synthesis of (+)-Guaymasol SN - 0936-5214 SN - 1437-2096 PY - 2014 JO - Synlett JF - Synlett LA - EN VL - 25 IS - 20 SP - 2883 EP - 2886 ET - 2014/10/17 DA - 2014/12/02 KW - natural products KW - total synthesis KW - cross-metathesis KW - dihydroxylation KW - phenols AB - The synthesis of (+)-guaymasol has been achieved from O-methyl chavicol by using a sequence combining a cross-metathesis and an asymmetric dihydroxylation of the newly created double bond. The first step using Grubbs type II catalyst delivered an inseparable 88:12 mixture of E and Z isomers. After treatment with AD-mix-β and deprotection of the benzyl ether by hydrogenolysis, (+)-guaymasol was finally isolated in 84% de and 90% ee. PB - © Georg Thieme Verlag DO - 10.1055/s-0034-1379480 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0034-1379480 ER -