The total synthesis of aristolindiquinone

Master Thesis

1986

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http://hdl.handle.net/11427/22134
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thesis_sci_1986_botha_marc_edgar.pdf (1.89 MB)
Authors
Botha, Marc Edgar
Supervisors
Giles, Robin G F
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University of Cape Town

Department
Department of Chemistry
Faculty
Faculty of Science
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Abstract
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).
Description

Bibliography: pages 97-99.

Keywords
Chemistry

Reference:

Botha, M. 1986. The total synthesis of aristolindiquinone. University of Cape Town.

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