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Synthesis of cis hexahydrobenzopyranones: bicyclic precursor lactones to the trichothecenes

Tetrahedron 46(3): 957-966

Synthesis of cis hexahydrobenzopyranones: bicyclic precursor lactones to the trichothecenes

Synthesis of bicyclic lactones 4-6, potential precursors to trichothecenes is described. These incorporate the cis AB ring juncture and double bond in proper position in ring A. Luche reduction of 7 followed by hydrolysis furnished lactone 9. Reaction of 7 with MeMgI and subsequent hydrolysis led to lactone 11 and was transformed to 4. Reduction of 14 and hydrolysis produced pyran carboxylic acid 15 which was converted to 20. Protection as epoxide 21 and oxidation with RuO4 furnished epoxylactone 22. Attempted deoxygenation afforded 5 which could not be obtained in pure form. Hydrolysis of primary ester in 14 and reduction of the sodium salt and subsequent acid treatment afforded lactone 6 and was converted to unsaturated lactone 23.

Accession: 001962555

DOI: 10.1016/s0040-4020(01)81375-2

Download PDF Full Text: Synthesis of cis hexahydrobenzopyranones: bicyclic precursor lactones to the trichothecenes

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