A NEW ACCESS TO TRANS-SYN-TRANS PERHYDROPHENANTHRENIC SYSTEMS - SYNTHESIS OF (9-BETA-H)-8-ALPHA-METHYLPODOCARPAN-13-ONE

Authors
WEIBEL JM HEISSLER D
Citation
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
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
3
Year of publication
1994
Pages
473 - 476
Database
ISI
SICI code
0040-4039(1994)35:3<473:ANATTP>2.0.ZU;2-R
Abstract
(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.