117180-06-0Relevant academic research and scientific papers
Preparation of oxocanes by electrophilic cyclizations of unsaturated alcohols in the presence of bis(collidine)halonium(I) hexafluorophosphates
Mendes, Christelle,Renard, Sylvie,Rofoo, Mazin,Roux, Marie-Claude,Rousseau, Gerard
, p. 463 - 471 (2007/10/03)
7-Octen-1-ols substituted in the sp3-sp3 carbon chain with carbocyclic (phenyl and cyclopropane) and heterocyclic (epoxide and dioxolane) moieties were prepared and their cyclizations in the presence of bis(collidine)iodonium(I) and-bromonium(I) hexafluorophosphates as electrophiles were studied. Oxocanes were obtained in modest to good yields when a rigid cyclic moiety (cyclopropane or phenyl) was present in the chain, while yields of cyclizations were lower if the cyclic component had a certain flexibility (dioxolane). Low yields were obtained with substrates bearing an epoxide substituent, probably because of stability problems due to the presence of collidine. With the vinylcyclopropane alcohol 12 we observed mainly the opening of the cyclopropane ring and the cyclization produced a tetrahydropyran derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Isomer Selectivity in Stereocontrolled Payne Rearrangement-epoxide Cleavage of 2,3-Epoxy Alcohols in Aprotic Solvents: Application to an Enantioselective Total Synthesis of (+)-exo-Brevicomin
Page, Philip C. Bulman,Rayner, Christopher M.,Sutherland, Ian O.
, p. 1375 - 1382 (2007/10/02)
Organo-copper and -cuprate reagents may be used to trap the more reactive epoxy alkoxide isomer in a Lewis acid-catalysed Payne rearrangement process.This methodology has been used as the key step in a five-step enantioselective total synthesis of (+)-exo
PROSTANOIDS. VIII. PRODUCTION OF C7-SYNTHONS USED IN THE SYNTHESIS OF LEUCOTRIENES
Miftakhov, M. S.,Tolstikov, A. G.,Tolstikov, G. A.
, p. 618 - 622 (2007/10/02)
On the basis of the obtainable 2E,7-octadienol and its acetate and benzoate preparative methods were developed for the production of methyl 7-hydroxy-5S,6S-epoxyheptanoate and methyl 6-formyl-5S,6S-epoxyhexanoate, which are used as synthons for leucotrienes.
