IMDA Reactions of β,δ-Diketoester-Substituted 1,7,9-Undecatrienes: Application­ in the Formal Synthesis of Solanapyrone D

Abstract

In this paper we describe the synthesis of β,δ-diketoester substituted 1,7,9-undecatrienes and their intramolecular Diels-Alder (IMDA) cycloadditions under thermal and acid-catalysed conditions. Application of this chemistry in the synthesis of a solanapyrone D precursor is reported.

Key words

intramolecular Diels-Alder reaction - polyketide - solanapyrone D

References

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2

Two different structures have been assigned the name solanapyrone E, [1] here we use the notation E and E′ to distinguish them.

9

For discussion of the thermal Diels-Alder chemistry of 1,7,9-trienes, see ref. 5 and references cited therein.

10

Compounds 3a-d were all prepared from (6E,8E)-deca-6,8-dienal. [15] See experimental section for further details.