Efficient synthesis of the tetracyclic aminoquinone moiety of marmycin A.
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.
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Nathan
N
Maugel
Barry B
BB
Snider
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry
D000880:Anthraquinones; D001688:Biological Products; C524224:marmycin A