Synthesis of Homoallylic Chiral Tertiary Alcohols via Chelation-Controlled Diastereoselective Nucleophilic Addition on α-Alkoxyketones: Application for the Synthesis of the C_1-C_(11) Subunit of 8-epi-Fostriecin

摘要

Chiral β-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti-homoallylic tertiary alcohols. This methodology has been applied for the synthesis of the C_1-C_(11) subunit of C_8-epi-fostriecin.