19926-46-6Relevant academic research and scientific papers
1,n-rearrangement of allylic alcohols promoted by hot water: Application to the synthesis of navenone B, a polyene natural product
Li, Pei-Fang,Wang, Heng-Lu,Qu, Jin
, p. 3955 - 3962 (2014/05/20)
It was reported for the first time that hot water as a mildly acidic catalyst efficiently promoted 1,n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C-C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction, a 1,3-rearrangement of the resulting allylic alcohol, and subsequent oxidation of the rearranged product.
Mild and tunable benzoic acid catalysts for rearrangement reactions of allylic alcohols
McCubbin, J. Adam,Voth, Samantha,Krokhin, Oleg V.
experimental part, p. 8537 - 8542 (2011/12/14)
An efficient and simple catalytic method for the isomerization of readily prepared allylic alcohols is described. We focus particularly on cyclic examples and the synthesis of unusual enyne and dienols. The benzoic acid catalysts employed are commercially available and very inexpensive and can be tuned for reactivity and substrate sensitivity.
Discovery of orally efficacious melanin-concentrating hormone receptor-1 antagonists as antiobesity agents. Synthesis, SAR, and biological evaluation of bicyclo[3.1.0]hexyl ureas
McBriar, Mark D.,Guzik, Henry,Shapiro, Sherry,Paruchova, Jaroslava,Xu, Ruo,Palani, Anandan,Clader, John W.,Cox, Kathleen,Greenlee, William J.,Hawes, Brian E.,Kowalski, Timothy J.,O'Neill, Kim,Spar, Brian D.,Weig, Blair,Weston, Daniel J.,Farley, Constance,Cook, John
, p. 2294 - 2310 (2007/10/03)
Melanin-concentrating hormone (MCH) is a cyclic, nonadecapeptide expressed in the CNS of all vertebrates that regulates feeding behavior and energy homeostasis via interaction with the central melanocortin system. Regulation of this interaction results in
Efficient and practical synthesis of both enantiomers of 3-phenylcyclopentanol derivatives
Okumura, Yoshiyuki,Ando, Akemi,William Stevens, Rodney,Shimizu, Makoto
, p. 8729 - 8736 (2007/10/03)
An efficient, multigram scale synthesis of the respective optical isomers of 3-(substituted-phenyl) cyclopentanols was achieved by a lipase-catalyzed transesterification (kinetic resolution) in organic medium. This enzymatic reaction proceeded with great
Formation of 1-Phenyl-2,3-dioxabicycloheptane in the Reaction of 1,3-Dibromo-4-phenylcyclopentane with Hydrogen Peroxide in the Presence of Silver Trifluoroacetate
Takahashi, Kimio,Shiro, Motoo,Kishi, Morio
, p. 3098 - 3104 (2007/10/02)
Reaction of 1,3-dibromo-4-phenylcyclopentane (23), prepared from 4-hydroxycyclopent-2-en-1-one (10) in a stereocontrolled manner, or its stereoisomer 24 with anhydrous hydrogen peroxide in the presence of silver trifluoroacetate in ether gave 1-phenyl-2,3-dioxabicycloheptane (25) mainly as a rearranged product.The expected 5-phenyl-2,3-dioxabicycloheptane (8) and phenylcyclopentenyl hydroperoxides 26 and 27 were also formed in this reaction.An authentic sample of endoperoxide 8 was prepared by using peroxide transfer reaction between bis(tri-n-butyltin)peroxide and bistriflate of cis-diol 35.The stereochemistry of the endoperoxide 8 and related compounds in this series was confirmed by correlation with the data from X-ray crystallographic analysis of the diacetate of diol 21 obtained from endoperoxide 8 by stannous chloride reduction.
