Stereoselective Total Synthesis of Tarchonanthuslactone and Formal Synthesis of (-)-Colletol

Abstract

A simple and efficient stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol is described using as the key steps Jacobsen’s kinetic resolution and a Sharpless asymmetric epoxidation. The synthesis of tarchonanthuslactone and the seco acid proceeded in 14% and 13% overall yield, respectively, starting from chiral (R)-propylene oxide.

Keywords

hydrolytic kinetic resolution - PMB acetal formation - Sharpless asymmetric epoxidation - lactonization - one-pot oxidation/alkenation - esterification

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12

(R)-Propylene oxide(6) was obtained by a literature procedure [Co(OAc)(R,R-Salen) (0.003 equiv), distd H₂O (0.55 equiv.), 0 °C, 12 h, yield: 47% of 6, 48% of (S)-propane-1,3-diol]¹⁰ and is easily isolated from the more polar diol (S)-propane-1,3-diol by distillation. Compound 6: [α]₂₅ ^D +11.6 (neat) {Lit.¹⁰ (S)-propylene oxide [α]₂₅ ^D -11.7 (neat)}.