Synthesis of deuterated methylenecyclohexanes, methylenedecalins and taraxasterols

✍ Scribed by Hsiu-Pu Daniel Lee; Larry S. Eichmeier; David M. Piatak

• Book ID: 102370791
• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: French
• Weight: 425 KB
• Volume: 20
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580201211

✦ Synopsis

T a r a x a s t e r o l s s p e c i f i c a l l y l a b e l l e d at various ring E sites w e r e synthesized as were cyclohexanes and decalins substituted by a methyl group and an erocyclic methylene m o i e t y similar to the ring E system of this terpene. Preparation of deuterated analogs in which the deuterium is located beta to the e x o c y c l i c d o u b l e b o n d w a s a c c o m p l i s h e d by catalytic reduction of the corresponding unsaturated ketone, followed by removal of the label at the alpha carbon and introduction of the exocyclic methylene with a Wittig reaction. Compounds labelled on the exocyclic methylene moiety were afforded by a Wittig reaction of the appropriate ketone with (methyl-d3)triphenylphosphonium bromide. Taraxasterol trideuterated alpha to the double bond was prepared by DCl exchange of the ketone followed by a Wittig reaction.