NaBH4-mediated non-chemoselective reduction of α,β-unsaturated ketones of chalcones in the synthesis of flavans

Ofentse Mazimba, Ishmael B. Masesane, Runner R.T. Majinda

Research output: Contribution to journalArticle

Abstract

In this paper, the NaBH4 mediated reduction of both the C-C and C-O double bonds of chalcones and subsequent acid mediated cyclisation of the saturated alcohols to flavans is described. The chalcones were readily prepared from commercially
available acetophenone and salicylaldehyde derivatives. Through this sequence of reactions, 3’,4’-dimethoxyflavan and 3’,4’,8-trimethoxyflavan were prepared in good overall yields.
Original languageEnglish
Pages (from-to)79-81
Number of pages3
JournalTRENDS IN ORGANIC CHEMISTRY
Volume16
Publication statusPublished - Jan 14 2012

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Chalcones
Ketones
Cyclization
Alcohols
Derivatives
Acids
salicylaldehyde
acetophenone

Cite this

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title = "NaBH4-mediated non-chemoselective reduction of α,β-unsaturated ketones of chalcones in the synthesis of flavans",
abstract = "In this paper, the NaBH4 mediated reduction of both the C-C and C-O double bonds of chalcones and subsequent acid mediated cyclisation of the saturated alcohols to flavans is described. The chalcones were readily prepared from commerciallyavailable acetophenone and salicylaldehyde derivatives. Through this sequence of reactions, 3’,4’-dimethoxyflavan and 3’,4’,8-trimethoxyflavan were prepared in good overall yields.",
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NaBH4-mediated non-chemoselective reduction of α,β-unsaturated ketones of chalcones in the synthesis of flavans. / Mazimba, Ofentse; Masesane, Ishmael B.; Majinda, Runner R.T.

In: TRENDS IN ORGANIC CHEMISTRY, Vol. 16, 14.01.2012, p. 79-81.

Research output: Contribution to journalArticle

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T1 - NaBH4-mediated non-chemoselective reduction of α,β-unsaturated ketones of chalcones in the synthesis of flavans

AU - Mazimba, Ofentse

AU - Masesane, Ishmael B.

AU - Majinda, Runner R.T.

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AB - In this paper, the NaBH4 mediated reduction of both the C-C and C-O double bonds of chalcones and subsequent acid mediated cyclisation of the saturated alcohols to flavans is described. The chalcones were readily prepared from commerciallyavailable acetophenone and salicylaldehyde derivatives. Through this sequence of reactions, 3’,4’-dimethoxyflavan and 3’,4’,8-trimethoxyflavan were prepared in good overall yields.

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