Synthesis of intermediates related to 11-deoxyanthracyclinones

Peter N. Preston, Thomas Winwick, John O. Morley

Research output: Contribution to journalArticle

Abstract

A series of Diels-Alder adducts has been synthesised from 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetraone (5), and the naphthacene (9b) has subsequently been converted into the epoxides (9d) and (9e). Catalytic hydrogenolysis of the ethanonaphthacene (9a) gave after work-up in air the 6,11 -dione (11), whereas hydrogenolysis of the methanonaphthacene (9f) gave a condensed leuco quinizarin derivative (13). Catalytic hydrogenolysis of the ethylenedioxynaphthacene (9e) gave the partially reduced trihydroxy derivative (15), the structure of which was established by converting it in two steps into the known trione (6a). Compound (9e) was also transformed oxidatively into the condensed quinizarin derivative (16), and by base-promoted methylation into a compound believed to be the dione (6d); the latter was deprotected to give the trione (6e).

Original languageEnglish
Pages (from-to)39-43
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1985

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Hydrogenolysis
Derivatives
Methylation
Epoxy Compounds
Air
1,4-dihydroxyanthraquinone

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Preston, Peter N. ; Winwick, Thomas ; Morley, John O. / Synthesis of intermediates related to 11-deoxyanthracyclinones. In: Journal of the Chemical Society, Perkin Transactions 1. 1985 ; pp. 39-43.
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Synthesis of intermediates related to 11-deoxyanthracyclinones. / Preston, Peter N.; Winwick, Thomas; Morley, John O.

In: Journal of the Chemical Society, Perkin Transactions 1, 1985, p. 39-43.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of intermediates related to 11-deoxyanthracyclinones

AU - Preston, Peter N.

AU - Winwick, Thomas

AU - Morley, John O.

PY - 1985

Y1 - 1985

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AB - A series of Diels-Alder adducts has been synthesised from 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetraone (5), and the naphthacene (9b) has subsequently been converted into the epoxides (9d) and (9e). Catalytic hydrogenolysis of the ethanonaphthacene (9a) gave after work-up in air the 6,11 -dione (11), whereas hydrogenolysis of the methanonaphthacene (9f) gave a condensed leuco quinizarin derivative (13). Catalytic hydrogenolysis of the ethylenedioxynaphthacene (9e) gave the partially reduced trihydroxy derivative (15), the structure of which was established by converting it in two steps into the known trione (6a). Compound (9e) was also transformed oxidatively into the condensed quinizarin derivative (16), and by base-promoted methylation into a compound believed to be the dione (6d); the latter was deprotected to give the trione (6e).

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JF - Journal of the Chemical Society, Perkin Transactions 1

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