Jm. Weibel et D. Heissler, A NEW ACCESS TO TRANS-SYN-TRANS PERHYDROPHENANTHRENIC SYSTEMS - SYNTHESIS OF (9-BETA-H)-8-ALPHA-METHYLPODOCARPAN-13-ONE, Tetrahedron letters, 35(3), 1994, pp. 473-476
(9 beta H)-8 alpha-Methylpodocarpan-13-one has been synthesized from a
9,10-syn bicyclic precursor by a reaction sequence including an intra
molecular Horner-Wadsworth-Emmons reaction - to form (9 beta H)-podoca
rp-8(14)-en-13-one - and an hydroxy-directed cyclopropranation to intr
oduce the 8-methyl group on the less accessible alpha side of the mole
cule.