24048-40-6Relevant academic research and scientific papers
Terpenoids. IX. Permanganate Oxidation of Thujopsene. 2. Neutral Products
Nagahama, Shizuo,Tazaki, Masato
, p. 4175 - 4177 (2007/10/02)
Permanganate oxidation of thujopsene 1 in dry and aqueous acetone was reexamined with a careful separation of the neutral part of the products.In dry acetone, the major products were Δ9-thujopsen-8β- and 8α-ols (2 and 3) which easily decomposed to thujopsadiene 6.In aqueous acetone, 1 gave 8β-hydroxythujopsan-9-one 8 and thujopsane-8α,9α-diol 11 as main products, besides 8β,9β-diol 10, 8α-hydroxythujopsan-9-one 9, and epimeric allyl alcohols 2 and 3.The hydroxy ketone 8 was isomerized to a ring contracted compound, 4α-acetyl-4β-hydroxy-6α,10,10-trimethyltricyclo1,3>decane 4 during alumina chromatography. 8β,9-Epoxy-10-thujopsanone 5 was isolated as a minor product.Kawamura's glycol was an eutectic mixture of 10 and 11.
DICYANOANTHRACENE-SENSITIZED PHOTOOXYGENATION OF THUJOPSENE
Hatsui, Toshihide,Suzuki, Nobumasa,Takeshita, Hitoshi
, p. 639 - 642 (2007/10/02)
9,10-Dicyanoanthracene-sensitized photooxygenation of thujopsene proceeded by singlet oxygen, but the reaction with added biphenyl caused an electron transfer and produced a novel product which has no longer possessed the cyclopropane ring.The ring cleavage is best explained in terms of intermediary formation of a radical cation.
PYROLYSIS OF 2-ALLYLOXYTROPONES: A NEW ELIMINATION RECTION TO TERMINAL DIENES
Takeshita, Hitoshi,Mametsuka, Hiroaki,Uchida, Kingo
, p. 1061 - 1064 (2007/10/02)
By pyrolysis over 140 deg C, several 2-alkenyloxytropones gave terminal dienes and regenerated tropolones.The elimination proceeded in the electrocyclic 6?+2?+2?-mode on the Claisen intermediates.This was applied to a synthesis of thujopsadiene.
