A stereocontrolled total synthesis of methyl (+/-)-O-methylpodocarpate

Roy, A. , Paul, T. , Drew, M.G.B. and Mukherjee, D. (2003) A stereocontrolled total synthesis of methyl (+/-)-O-methylpodocarpate. Tetrahedron Letters, 44 (26). pp. 4835-4837. ISSN 0040-4039 doi: 10.1016/S0040-4039(03)01124-9

Abstract/Summary

A stereocontrolled total synthesis of methyl (+/-)-O-methyl podocarpate (4) has been successfully accomplished using the trans-fused diester 21 as a key intermediate. Intramolecular Michael reaction of the enone-diester 18 afforded the cis-fused keto-diester 19 in high yield which was stereoselectively converted into 21 via the enone 20. (C) 2003 Elsevier Science Ltd. All rights reserved.