The total synthesis of aristolindiquinone

Aristolindiquinone (1), a novel natural compound possibly: possessing anti-fertility activity, was synthesized via two independent routes. First, a Stobbe reaction unambiguously gave the naphthalene nucleus with the required substitution pattern (3,8-dioxygenated-2,5-dimethyl naphthalene), starting from 2-hydroxy-5-methylbenzaldehyde (31). Second, a general synthesis, of substituted C-5 oxygenated- 1,4-naphthoquinones is applied to the synthesis of (1). The critical step in the synthesis is the reaction of the novel Diels-Alder partners, dienophile (90), synthesized from 2,6-dihydroxytoluene (56), and diene (109).

Grantor dc:publisher.institution

Department of Chemistry

Year dc:date.issued

1986

Author dc:creator

• Botha, Marc Edgar

Advisor dc:contributor.advisor

• Giles, Robin G F

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/11427/22134

OAI identifier oai:identifier

oai:open.uct.ac.za:11427/22134