201472-65-3Relevant academic research and scientific papers
Synthesis of sabina δ-lactones and sabina δ-lactams from (+)-sabinene
Gnilka, Radoslaw,Wawrzenczyk, Czeslaw
, p. 1399 - 1405 (2013/12/04)
Two sabina δ-lactones (3 and 4) were obtained in a two-step synthesis from (+)-sabinene (1). The oxidation of (+)-sabinene (1) with potassium permanganate and sodium periodate to (-)-sabina ketone (2) was the first step. In the second step, the ketone obtained was subjected to chemical and microbial Baeyer-Villiger oxidation. Chemical Baeyer-Villiger oxidation of this ketone afforded two δ-lactones 3 and 4 whereas microbial Baeyer-Villiger oxidation afforded only 'abnormal' δ-lactone 4. (-)-Sabina ketone was also the starting material for the synthesis of new δ-lactams (7 and 8). They were obtained by Beckmann rearrangement of sabina ketone oximes 5a and 5b. An attempt to separate (-)-sabina ketone oximes 5a and 5b is also presented. CSIRO 2013.
