NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans

Ishmael B. Masesane; Ofentse Mazimba

doi:10.1007/978-94-007-7389-9_16

NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans

Ishmael B. Masesane, Ofentse Mazimba

Botswana International University of Science & Technology

Research output: Chapter in Book/Report/Conference proceeding › Chapter

Abstract

In this chapter, the NaBH₄-mediated reduction of both the carbon-carbon double bond and the carbonyl group of chalcones and subsequent acid mediated cyclisation of the resulting 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 language	English
Title of host publication	Chemistry
Subtitle of host publication	The Key to our Sustainable Future
Publisher	Springer Netherlands
Pages	229-235
Number of pages	7
ISBN (Electronic)	9789400773899
ISBN (Print)	9789400773882
DOIs	https://doi.org/10.1007/978-94-007-7389-9_16
Publication status	Published - Jan 1 2014

All Science Journal Classification (ASJC) codes

Environmental Science(all)

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10.1007/978-94-007-7389-9_16

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AB - In this chapter, the NaBH4-mediated reduction of both the carbon-carbon double bond and the carbonyl group of chalcones and subsequent acid mediated cyclisation of the resulting 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.

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NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans

Abstract

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