Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Experiments on the synthesis of tetracycline. Part 16. Improved photocyclic preparation of 12-keto-derivatives and their deprotection using benzeneseleninic anhydride

Derek H. R. Barton,   Maria T. Bielska,   José M. Cardoso,   Nigel J. Cussans  and  Steven V. Ley  

Abstract

Improved methods for the photocyclisation of 4-[2-(1,3-dithiolan-2-yl)benzyl]-2-phenylnaphtho[1,8-bc]furan-5-one (6; X = Y = S) and 4-[2-(1,3-dithiolan-2-yl)-3,5-dihydroxy-4-methoxycarbonylbenzyl]-2-phenylnaphtho[1,8-bc]furan-5-one (1; X = Y = S) to their tetracyclic analogues are described. Deprotection of the C-12 thioacetal unit in the cyclised products was achieved using benzeneseleninic anhydride. Introduction of a 6α-methyl substituent and an amide grouping into C-2 of certain tetracyclic substrates provides compounds which have potential use for tetracycline synthesis.

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Article information

DOI
https://doi.org/10.1039/P19810001840
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1840-1845

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Experiments on the synthesis of tetracycline. Part 16. Improved photocyclic preparation of 12-keto-derivatives and their deprotection using benzeneseleninic anhydride

D. H. R. Barton, M. T. Bielska, J. M. Cardoso, N. J. Cussans and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1981, 1840 DOI: 10.1039/P19810001840

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