Issue 0, 1973
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Marine natural products of the Atlantic zone. Part VI. Base-catalysed rearrangement of taondiol

Antonio G. González,   Miguel A. Alvarez,   José Darias  and  Julio D. Martín  

Abstract

The base-catalysed isomerisation of taondiol (1; R1= R2= H), an aromatic terpenoid containing the 1H-naphtho[2,1-a]xanthen skeleton recently isolated from the marine alga Taonia atomaria(Dyctiotaceae), into its C-6a methyl epimer (2) has been studied. A free-radical mechanism is proposed for the reaction. Base-catalysed methyl inversion at C-6a was also carried out on 2-deoxy-9,11-dimethyltaondiol (21; R = H), prepared by condensation of (13R)-labda-8(20),14-dien-13-ol (18) with trimethylhydroquinone (19) and subsequent cyclisation.

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Article information

DOI
https://doi.org/10.1039/P19730002637
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 2637-2642

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Marine natural products of the Atlantic zone. Part VI. Base-catalysed rearrangement of taondiol

A. G. González, M. A. Alvarez, J. Darias and J. D. Martín, J. Chem. Soc., Perkin Trans. 1, 1973, 2637 DOI: 10.1039/P19730002637

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