Synthesis of the 5-thiorotenoid system from thiochroman-3-one

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Base-induced cyclisation of the diketones 10 (X = H or F), prepared in a two-step sequence from thiochroman-3-one, affords 6H,12H-[1]benzothiopyrano[3,4- b][1]benzopyran-12-ones 11. Reduction with diisobutylaluminium hydride affords a separable mixture of the cis- and trans-5-thiorotenoids. Dieckmann cyclisation of ethyl 2-(ethoxycarbonylmethylthio)phenylethanoate affords a mixture of 4-ethoxycarbonyl- and 2-ethoxycarbonyl-thiochroman-3-ones. Attempts to prepare a thiorotenoid by condensation of these β-keto esters with 4-methoxyphenol resulted in formation of the novel bis[1]benzothiopyrano[3,2-b:4′, 3′-e]pyran ring system.

LanguageEnglish
Pages3015-3018
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number22
DOIs
Publication statusPublished - 1 Dec 1992
Externally publishedYes

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Cyclization
Benzopyrans
Pyrans
Condensation
Esters
diisobutylaluminum
mequinol

Cite this

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title = "Synthesis of the 5-thiorotenoid system from thiochroman-3-one",
abstract = "Base-induced cyclisation of the diketones 10 (X = H or F), prepared in a two-step sequence from thiochroman-3-one, affords 6H,12H-[1]benzothiopyrano[3,4- b][1]benzopyran-12-ones 11. Reduction with diisobutylaluminium hydride affords a separable mixture of the cis- and trans-5-thiorotenoids. Dieckmann cyclisation of ethyl 2-(ethoxycarbonylmethylthio)phenylethanoate affords a mixture of 4-ethoxycarbonyl- and 2-ethoxycarbonyl-thiochroman-3-ones. Attempts to prepare a thiorotenoid by condensation of these β-keto esters with 4-methoxyphenol resulted in formation of the novel bis[1]benzothiopyrano[3,2-b:4′, 3′-e]pyran ring system.",
author = "Gabbutt, {Christopher D.} and Hepworth, {John D.} and Heron, {B. Mark}",
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Synthesis of the 5-thiorotenoid system from thiochroman-3-one. / Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 22, 01.12.1992, p. 3015-3018.

Research output: Contribution to journalArticle

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AU - Gabbutt, Christopher D.

AU - Hepworth, John D.

AU - Heron, B. Mark

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AB - Base-induced cyclisation of the diketones 10 (X = H or F), prepared in a two-step sequence from thiochroman-3-one, affords 6H,12H-[1]benzothiopyrano[3,4- b][1]benzopyran-12-ones 11. Reduction with diisobutylaluminium hydride affords a separable mixture of the cis- and trans-5-thiorotenoids. Dieckmann cyclisation of ethyl 2-(ethoxycarbonylmethylthio)phenylethanoate affords a mixture of 4-ethoxycarbonyl- and 2-ethoxycarbonyl-thiochroman-3-ones. Attempts to prepare a thiorotenoid by condensation of these β-keto esters with 4-methoxyphenol resulted in formation of the novel bis[1]benzothiopyrano[3,2-b:4′, 3′-e]pyran ring system.

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