84367-90-8Relevant articles and documents
Tobacco Chemistry. 56. The Stereochemistries of the Tobacco Diterpenoids: The (1S,2E,4S,6E,8S,11E)- and (1S,2E,4R,6E,8S,11E)-2,6,11-Cembratriene-4,8-diols. Acid-induced Transformations of Cembratrienediols
Wahlberg, Inger,Behr, Dan,Eklund, Ann-Marie,Nishida, Toshiaki,Enzell, Curt R.,Berg, Jan-Eric
, p. 443 - 450 (2007/10/02)
The stereochemistries of the (1S,2E,4S,6E,8S,11E)- and (1S,2E,4R,6E,8S,11E)-2,6,11-cembratriene-4,8-diols (1, 2) have been determined by X-ray analysis.Acid-induced transformations of the 4,8-diols (1, 2) and the (1S,2E,4S,6R,7E,11E)- and (1S,2E,4R,6R,7E,11E)-cembratriene-4,6-diols (3, 4) have been studied.The results show that the 4S,6R- and 4R,6R-diols (3, 4) are interconvertible with the 4S,8S- and 4S,8R-diols (1, 7) and with the 4R,8S-diol (2), respectively.The 4,6-diols (3, 4) also undergo epimerization reactions and a fragmentation reaction yielding a seco-aldehyde (6).