Highly efficient, enantioselective synthesis of (+)-grandisol from a C<inf>2</inf>-symmetric bis(α,β-butenolide)

Pedro De March, Marta Figueredo, Josep Font, Javier Raya

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47 Citations (Scopus)

Abstract

(equation presented) A new, very efficient, enantioselective synthesis of the sexual attracting insect pheromone (+)-grandisol has been developed, in which the key step is the double [2 + 2] photocycloaddition of ethylene to a bis(α,beta;-butenolide) readily available from D-mannitol. The C2symmetry of the substrate and the appropriate protection of the central diol unit are the crucial features for the high diastereofacial discrimination during the cycloaddition process.
Original languageEnglish
Pages (from-to)163-165
JournalOrganic Letters
Volume2
Issue number2
Publication statusPublished - 27 Jan 2000

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