Facile Total Synthesis of Carbonolides by Witting-Hoener Macro-Cyclization and Stereoselective Epoxidation

摘要: Sixteen-membered dienone type macrolide aglycons, carbonolide B (1), niddanolide (5), and platenolide W1 (6), were synthesized highly stereoselectively from D-glucose via Yamaguchi's esterification of two fragments, 8 (C1-C10) 9 (C11-C16), followed by Witting-Horner cyclization. Stereoselective epoxidation the 16-membered dienones (34, 35) gave epoxy-enone-type A (2) EOP aglycon (7).