Browsing by Author "Botha, Marc Edgar"

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    The total synthesis of aristolindiquinone
    (1986) Botha, Marc Edgar; Giles, Robin G F
    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).