Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix
We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described. Copyright
Rogers, Erik,Araki, Hiroshi,Batory, Lindsay A.,McInnis, Christine E.,Njardarson, Jon T.
p. 2768 - 2769
(2007/10/03)
PRODUCTION OF 2,5-DIHYDROFURANS AND ANALOGOUS COMPOUNDS
Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-l-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate
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Page/Page column 33
(2008/06/13)
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