174757-07-4Relevant academic research and scientific papers
Further explorations into the synthesis of Dehydro-Hedione
Winter, Béat,Chapuis, Christian,Brauchli, Robert,De Saint Laumer, Jean-Yves
, p. 246 - 258 (2013/03/28)
Dehydrohedione (DHH) 1 may be obtained in 20% overall yield by a Reformatsky reaction with enone methyl ether 3b, followed by acidic workup of the crude reaction mixture. Alternatively, epoxidation (3-chloroperbenzoic acid, CH2Cl2, 84% yield) of the tertiary allyl alcohol derivative 4 affords a 1: 2 mixture of 8a and 8b. The latter epoxy ester 8b may also be obtained stereoselectively either from 4 (tBuO2H, [Mo(CO)6], 1,2-dichloroethane, 70°, 62% yield; or tBuO2H, [VO(acac)2], decane, 20°, 92% yield), or from 5 (AcOMe, LiN(SiMe3)2, THF, -78°, 84-87%). BF3×Et2O-Catalyzed cascade rearrangement and OH elimination of 8a afford selectively DHH 1 in 88% yield. The cis disposition of the side chains of the weakly odoriferous hedione-like analogues 2b and 2c was maintained by means of either an epoxy or a cyclopropane moiety. Copyright
