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Efficient synthesis of the tetracyclic aminoquinone moiety of marmycin A.

ABSTRACT: An efficient four-step route to the tetracyclic aminoquinone moiety of marmycin A that proceeds in 41% overall yield from 5-nitronaphthoquinone and 5-methyl-1-vinylcyclohexene will facilitate preparation of marmycin A analogues for biological evaluation. The Diels-Alder reaction gave exclusively the desired adduct that is favored by steric considerations rather than the regioisomeric adduct that is favored by electronic considerations.

SUBMITTER: Maugel N

PROVIDER: S-EPMC2784112 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Efficient synthesis of the tetracyclic aminoquinone moiety of marmycin A.

Maugel Nathan N Snider Barry B BB

Organic letters 20091101 21

An efficient four-step route to the tetracyclic aminoquinone moiety of marmycin A that proceeds in 41% overall yield from 5-nitronaphthoquinone and 5-methyl-1-vinylcyclohexene will facilitate preparation of marmycin A analogues for biological evaluation. The Diels-Alder reaction gave exclusively the desired adduct that is favored by steric considerations rather than the regioisomeric adduct that is favored by electronic considerations. ...[more]

PMID: 19803528

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