Unified Approach for the Total Synthesis of Bis-THF C15 Acetogenins: A Chloroenyne from Laurencia majuscula, Laurendecumenyne B and Laurefurenynes A/B

Abstract

AbstractA highly diastereoselective total synthesis of several bis-THF C15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenynes A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, SN2 halo­genation, and a relay cross metathesis.