Massoia lactone, synthesis

The dianion derived from but-2-ynoic acid reacts with aldehydes to give 5-hydroxyalk-2-ynoates (539). Partial reduction over a Lindlar catalyst and acid-catalyzed cyclization of the resulting enoate gives the dihydropyran-2-one (78LA337). The route is exemplified by the synthesis of the naturally occurring massoia lactone (Scheme 200). In previous work (46JCS954) the hydroxyalkynoic acids themselves, obtained from epoxides and acetylene, were used. 

Synthesis of goniothalamin, massoia lactone, and parasorbic acid... 

Next to these fatty acids, hydroxy fatty acids can be used as substrates for 8-lactone synthesis via biotransformation in bacterial cells. Clostridium tyrobutyricum uses 5-hydroxy-2-decenoic acid or 5-hydroxy-2-dodecenoic acid to produce 8-decalactone (5.95 gL ) or 8-dodecalactone (13 gL ) (Pichersky 1998). Bacillus subtilis and Pseudomonas sp. transform massoia lactone to 8-decalactone (Gocho et al. 1998). Therefore, in case of y-DL, 8-decalactone, and 8-dodecalactone, the hurdle to achieve product concentrations far above 100 mg can be overcome by screening and choice of appropriate... 

---