The Synthesis of a Sulfone Containing Analogue of the Esperamicin-A1 Aglycone: A Hetero Diels-Alder Approach

Jaya Prabhakaran; Hervé Lhermitte; Jagattaran Das; T. K. Sasi-Kumar; David S. Grierson

doi:10.1055/s-2000-6602

Synlett 2000; 2000(5): 0658-0662
DOI: 10.1055/s-2000-6602

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The Synthesis of a Sulfone Containing Analogue of the Esperamicin-A₁ Aglycone: A Hetero Diels-Alder Approach

Jaya Prabhakaran^* , Hervé Lhermitte, Jagattaran Das, T. K. Sasi-Kumar, David S. Grierson

^*Institut de Chimie des Substances Naturelles, C.N.R.S., 91198 Gif-sur-Yvette, France; Fax + 33(1)69 07 53 83; E-mail: david.grierson@curie.u-psud.fr

Abstract

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The hetero Diels-Alder reaction of methyl/ethyl thioglyoxylate, generated in situ from the corresponding anthracene adduct, with a series of dienes was studied as a route to a key 3,4-dihydro-2H-thiopyran derivative bearing an acetylene function at C-2, and hydroxyl groups at C-3 and C-4. Such a molecule is a planned intermediate in the synthesis of a sulfone containing analogue of esperamicin-A₁. In this context, particular attention was directed to the hetero Diels-Alder reaction with polyfunctionalized dienes substituted at C-1 by a latent aldehyde function, and at C-4, C-2 and/or C-3 by ether substituents.

enediyne - esperamicin-A1 - 2,dihydrothia-2H-pyran - hetero Diels-Alder reaction - thioaldehyde

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