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

Ishmael B. Masesane, Ofentse Mazimba

Research output: Chapter in Book/Report/Conference proceedingChapter

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 languageEnglish
Title of host publicationChemistry
Subtitle of host publicationThe Key to our Sustainable Future
PublisherSpringer Netherlands
Pages229-235
Number of pages7
ISBN (Electronic)9789400773899
ISBN (Print)9789400773882
DOIs
Publication statusPublished - Jan 1 2014

Fingerprint

ketone
carbon
alcohol
acid

All Science Journal Classification (ASJC) codes

  • Environmental Science(all)

Cite this

Masesane, Ishmael B. ; Mazimba, Ofentse. / NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans. Chemistry: The Key to our Sustainable Future. Springer Netherlands, 2014. pp. 229-235
@inbook{44fbfea8de4b4030b0ab5b8e68e8fd6c,
title = "NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans",
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.",
author = "Masesane, {Ishmael B.} and Ofentse Mazimba",
year = "2014",
month = "1",
day = "1",
doi = "10.1007/978-94-007-7389-9_16",
language = "English",
isbn = "9789400773882",
pages = "229--235",
booktitle = "Chemistry",
publisher = "Springer Netherlands",
address = "Netherlands",

}

NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans. / Masesane, Ishmael B.; Mazimba, Ofentse.

Chemistry: The Key to our Sustainable Future. Springer Netherlands, 2014. p. 229-235.

Research output: Chapter in Book/Report/Conference proceedingChapter

TY - CHAP

T1 - NaBH4-mediated complete reduction of the α,β-unsaturated ketone units of chalcones in the synthesis of flavans

AU - Masesane, Ishmael B.

AU - Mazimba, Ofentse

PY - 2014/1/1

Y1 - 2014/1/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84956716544&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84956716544&partnerID=8YFLogxK

U2 - 10.1007/978-94-007-7389-9_16

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

M3 - Chapter

SN - 9789400773882

SP - 229

EP - 235

BT - Chemistry

PB - Springer Netherlands

ER -