201472-64-2Relevant articles and documents
Synthesis of sabina δ-lactones and sabina δ-lactams from (+)-sabinene
Gnilka, Radoslaw,Wawrzenczyk, Czeslaw
, p. 1399 - 1405 (2013)
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.
Isolation of ozonides from gas-phase ozonolyses of terpenes
Griesbaum, Karl,Miclaus, Vasile,Jung, In Chan
, p. 647 - 649 (1998)
Ozonolyses of (-)-β-pinene (1) and of (+)-sabinene (6) in the gas phase afforded the corresponding ozonides 6,6- dimethylbicyclo[3.1.11,5]heptane[2-spiro-3]-1,2,4-trioxolane (2) and 5- isopropylbicyclo[3.1.01,5]hexane[2-spiro-3]1,2,4-trioxolane (7), which were isolated as mixtures of two diastereomers each. Major products were the corresponding ketones 6,6-dimethyl-2-oxobicyclo[3.1.11,5]heptane (3) and 5-isopropyl-2-oxobicyclo[3.1.01,5]hexane (8). Additional products were the lactones 7,7-dimethyl-2-oxa-3-oxobicyclo[4.1.11,6]octane (4) and 7,7- dimethyl-3-oxa-2-oxobicyclo[4.1.11,6]octane (5) derived from β-pinene (1) as well as 6-isopropyl-2-oxa-3-oxobicyclo[4.1.01,6]heptane (9) and 6- isopropyl-3-oxa-2-oxobicyclo[4.1.01,6]heptane (10) derived from sabinene (6). Ozonolyses of (-)-β-pinene (1) and of (+)-sabinene (6) in the gas phase afforded the corresponding ozonides 6,6-dimethylbicyclo[3.1.11,5]heptane[2-spiro-3]-1, 2,4-trioxolane (2) and 5-isopropylbicyclo[3.1.01,5]hexane [2-spiro-3]-1,2,4-trioxolane (7), which were isolated as mixtures of two diastereomers each. Major products were the corresponding ketones 6,6-dimethyl-2-oxobicyclo[3.1.11,5]heptane (3) and 5-isopropyl-2-oxobicyclo[3.1.01,5]hexane (8). Additional products were the lactones 7,7-dimethyl-2-oxa-3-oxobicyclo[4.1.11,6]octane (4) and 7,7-dimethyl-3-oxa-2-oxobicyclo[4.1.11,6]octane (5) derived from β-pinene (1) as well as 6-isopropyl-2-oxa-3-oxobicyclo[4.1.01,6]heptane (9) and 6-isopropyl-3-oxa-2-oxobicyclo[4.1.01,6]heptane (10) derived from sabinene (6).
