40768-86-3Relevant academic research and scientific papers
Concomitant bromination and lactolisation of unsaturated diols with sodium bromite in aqueous acetic acid
Evans, Gary B.,Grant, Peter K.
, p. 4709 - 4712 (2007/10/03)
The attempted lactonisation of unsaturated diols 8, 13, and 15 using sodium bromite in aqueous acetic acid gave the bromo lactols 9, 16, and 18 respectively. The bromo lactols were converted to their corresponding lactones 10, 17, and 19 using Jones reagent.
Photosensitized Oxygenation of Labda-8(17),12-diene, Labda-8(17),13-diene, and the Biformenes. Synthesis of Pumiloxide
Mohanraj, Subramaniam,Herz, Werner
, p. 1362 - 1366 (2007/10/02)
Reactions of the title compounds with singlet oxygen were studied.In labda-8(17),12-diene (2; 7:3 mixture of E and Z isomers), syn addition leading to 7 (58percent) was predominant.Smaller amounts of 8 (20percent) by syn addition to (E)-2 or anti addition to (Z)-2, 9 (5percent), 10 (2,5percent), and 11(1.5percent) were also formed. (E)-Labda-8(17),13-diene ((E)-3) gave 29percent 12 and 40percent 13 by syn addition, whereas (Z)-3 gave 57percent 12 by syn addition and 19percent 13 by anti addition.In trans-biformene (5) syn attack at C-12 to give 15 (27percent), 16 (10percent), 18 (12percent), and 19 (4percent) was greatly preferred to syn attack at C-13 to give 17 (6percent).In cis-biformene (6) syn attack at C-13 to give 17 (39percent) predominated slightly over anti attack at C-12 to give 15 (13percent), 16 (8percent), 18 (4percent), and 19 (4percent).Diels-Alder reactions with singlet oxygen leading to epidioxides 20 and 21 were relatively unimportant (7percent from 5, 5percent from 6).The epidioxides were converted to the naturally occurring furanolabdane pumiloxide (22).
