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Diels-Alder reaction of maldoxin with an isopropenylallene.

ABSTRACT: The Diels-Alder reaction of maldoxin with an isopropenylallene at 60-75 °C afforded an adduct closely related to chloropestolide A (24%) and a second adduct (0-11%) that underwent an ene reaction to generate the chloropupukeanolide D (11-22%) skeleton. The Diels-Alder reaction occurred with good selectively (>5:1) from a single face of maldoxin under much milder conditions than previously reported for the analogous dimethoxycyclohexadienone. Furthermore, the ene reaction took place under mild conditions whereas the analogous Diels-Alder adduct from the dimethoxycyclohexadienone did not undergo an ene reaction.

SUBMITTER: Yu M

PROVIDER: S-EPMC3327307 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Diels-Alder reaction of maldoxin with an isopropenylallene.

Yu Min M Snider Barry B BB

Tetrahedron 20111004 49

The Diels-Alder reaction of maldoxin with an isopropenylallene at 60-75 °C afforded an adduct closely related to chloropestolide A (24%) and a second adduct (0-11%) that underwent an ene reaction to generate the chloropupukeanolide D (11-22%) skeleton. The Diels-Alder reaction occurred with good selectively (>5:1) from a single face of maldoxin under much milder conditions than previously reported for the analogous dimethoxycyclohexadienone. Furthermore, the ene reaction took place under mild co ...[more]

PMID: 22518065

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