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A Total Synthesis of the Styryllactone (+)-Goniodiol from Naphthalene

Banwell, Martin; Coster, Mark; Edwards, Alison; Karunaratne, Ochitha; Smith, Jason A; Welling, Lee; Willis, Anthony

Description

The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxidative cleavage to dialdehyde (7) followed by reduction to give diol (12). Conversion of compound (12) into acetal (17) required, inter alia, selective oxidation of the benzylic alcohol moiety followed by a metal-catalyzed decarbonylation of the...[Show more]

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
URI: http://hdl.handle.net/1885/88394
Source: Australian Journal of Chemistry
DOI: 10.1071/CH02242

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