132340-81-9Relevant academic research and scientific papers
SYNTHESYS AND STEREOCHEMISTRY OF 3,6-EPOXY-5-HYDROXY-5,6-DIHYDRO-β-IONOL, A NOVEL FLAVOR CONSTITUENT OF SUIFU TABACCO
Kato, Tetsuya,Kondo, Hisao,Kitano, Yukishige,Hata, Go,Takagi, Yoshikazu
, p. 757 - 760 (1980)
(+/-)-3,6-Epoxy-5-hydroxy-5,6-dihydro-β-ionol was synthesized from β-ionone via 3,6-dihydroxy-α-ionone and its structure including the relative configurations was established as (+/-)-2β,5β-epoxy-2α--1β,3,3-trimethylcyclohexan-1α-ol by X-ray analysis.
A New Rearrangement: Conversion of a Diepoxycyclohexane into a Dihydropyrancarbaldehyde
Moss, Gerard P.,Ooi, Cheng Keat
, p. 342 - 343 (2007/10/02)
Treatment of 2,7,7-trimethyl-3,8-dioxotricyclo2,4>octane 5 and derivatives with BF3 gave the corresponding 4,4,5-trimethyl-3,4-dihydro-2H-pyran-2-carbaldehyde 7 and traces only of 3,5,5-trimethyl-7-oxabicycloheptan-2-one 8.
Carotenoids with 7-Oxabicycloheptyl End Groups. Attempted Synthesis of Cycloviolaxanthin (=(3S,5R,6R,3'S,5'R,6'R)-3,6:3',6'-Diepoxy-5,6,5'6'-tetrahydro-β,β-carotin-5,5'-diol)
Gmuender, Michael Roman,Eugster, Conrad Hans
, p. 1954 - 1969 (2007/10/02)
Starting from our recently described synthon (+)-24, the enantiomerically pure 3,6:4,5:3',6':4',5'-tetraepoxy-4,5,4',5'-tetrahydro-ε,ε-carotene (34) and its 15,15'-didehydro analogue 32 were synthesized in eleven and nine steps, respectively (Scheme 4).Chiroptical data show, in contrast to the parent ε,ε-carotene, a very weak interaction between the chiral centers at C(5), C(5'), C(6), C(6'), and the polyene system.Diisobutylaluminium hydride reduction of 32 lead rather than to the expected 15,15'-didehydro analogue 35 of cycloviolaxanthin (8), to the polyenyne 36 (Scheme 5).We explain this reaction by an oxirane rearrangement leading to a cyclopropyl ether followed by a fragmentation to an aldehyd on the one side and an enol ether on the other (Scheme 6).This complex rearrangement includes a shift of the whole polyenyne chain from C(6), C(6') to C(5), C(5') of the original molecule.
