Synthesis of tritium-labelled cembrene-A

✍ Scribed by Ambarish K. Singh; Glenn D. Prestwich

• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: French
• Weight: 221 KB
• Volume: 23
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580230405

✦ Synopsis

Commiphora s a p ( 3 1 , s o f t c o r a l s ( 4 1 , termite s o l d i e r s (5-8), t e r m i t e workers (9-101, and a n t s (11).

Neither t h e b i o s y n t h e s i s of cembrene-A (presumably from g e r a n y l g e r a n y l pyrophosphate) nor i t s conversion i n t o any simple epoxide, d i o l , e t h e r , l a c t o n e , o r complex p o l y c y c l i c s t r u c t u r e has y e t been demonstrated i n v i v o or -i n v i t r o . b i o g e n e s i s of cembrenoids has been t h e absence of a r a d i o l a b e l l e d isotopomer f o r metabolic s t u d i e s . We r e p o r t h e r e i n a mild and s e l e c t i v e process f o r i n t r o d u c i n g a high s p e c i f i c a c t i v i t y t r i t i u m l a b e l a t C-16 ( t h e methylidene carbon). The method h a s g e n e r a l a p p l i c a b i l i t y t o t h e l a b e l l i n g of p o l y o l e f i n i c t e r p e n e hydrocarbons b e a r i n g a n i s o p r o p e n y l s i d e chain.