Synthesis 2007(23): 3639-3646  
DOI: 10.1055/s-2007-990850
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

J. S. Yadav*, P. Murali Krishna Reddy, Manoj K. Gupta, Ch. Janardhana Chary
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
Further Information

Publication History

Received 14 August 2007
Publication Date:
29 October 2007 (online)

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.

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)}.