Journal of the Chemical Society. Perkin transactions I p. 1096 - 1102 (1981)
Update date:2022-08-04
Topics:
Banks, Robert E.
Miller, Allen J.
Nunn, John M.
Stanley, Philip
Weakley, Timothy J. R.
Ullah, Zakir
2-Methyl-3-yn-2-ol (9) is efficiently converted into 6-formyl-3,6-dimethylcyclohex-2-enyl acetate (4b) and into 6-acetyl-3,6-dimethylcyclohex-2-enyl acetate (4c) via highly regio- and stereo-selective Diels-Alder cycloadditions of 3-methylbuta-1,3-dienyl acetate (2b).The cycloadduct (4b) is converted by base into 4a,5,6,8a-tetrahydro-4a,7-dimethylcoumarin (13b), whilst the cycloadduct (4c) yields 2,3,4a,5,6,8a-hexahydro-2-hydroxy-2,4a,7-trimethylchroman-4-one (15), the structure of which was confirmed by X-ray analysis.Both (13b) and (15) possess a number of structural features of the trichothecenes and may be of value in their total synthesis.
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