TY - JOUR AU - Mohammad, Shabbair; Dhambri, Sabrina; Gori, Didier; Vaxelaire, Carine; Sorin, Geoffroy; Ardisson, Janick; Lannou, Marie-Isabelle TI - Asymmetric Sharpless Dihydroxylation Reaction of Chiral Bishomoallylic Alcohols: Application to the Synthesis of the C1–C10–C5 Fragment of FR225654 SN - 0936-5214 SN - 1437-2096 PY - 2013 JO - Synlett JF - Synlett LA - EN VL - 24 IS - 19 SP - 2581 EP - 2585 ET - 2013/10/18 DA - 2013/11/20 KW - stereoselective synthesis KW - natural products KW - dihydroxy­lation KW - diols KW - diastereoselectivity AB - Toward the synthesis of FR225654, an antidiabetic natural product, the Sharpless asymmetric dihydroxylation of chiral bishomoallylic alcohols, never reported in the literature, was examined. Employing the pyrimidine class of ligands, a high level of matched diastereoselectivity was obtained. An application to the stereoselective synthesis of the C1–C10–C5 fragment of FR225654 was performed. PB - © Georg Thieme Verlag DO - 10.1055/s-0033-1340164 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0033-1340164 ER -