The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones

Christopher D. Gabbutt, John D. Hepworth, B. Mark Heron, Jean Luc Thomas

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones.

LanguageEnglish
Pages881-884
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number8
DOIs
Publication statusPublished - 19 Feb 1998
Externally publishedYes

Fingerprint

Chromans
2'-hydroxyacetophenone

Cite this

@article{6b4f0e74855e46a085f261abc4b7a6b9,
title = "The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones",
abstract = "Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones.",
author = "Gabbutt, {Christopher D.} and Hepworth, {John D.} and Heron, {B. Mark} and Thomas, {Jean Luc}",
year = "1998",
month = "2",
day = "19",
doi = "10.1016/S0040-4039(97)10646-3",
language = "English",
volume = "39",
pages = "881--884",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "8",

}

The oxidative ring expansion of spiro-annulated chroman-4-ones : Syntheses of the rotenoid core and related benzoxanthones. / Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark; Thomas, Jean Luc.

In: Tetrahedron Letters, Vol. 39, No. 8, 19.02.1998, p. 881-884.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The oxidative ring expansion of spiro-annulated chroman-4-ones

T2 - Tetrahedron Letters

AU - Gabbutt, Christopher D.

AU - Hepworth, John D.

AU - Heron, B. Mark

AU - Thomas, Jean Luc

PY - 1998/2/19

Y1 - 1998/2/19

N2 - Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones.

AB - Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones.

UR - http://www.scopus.com/inward/record.url?scp=0032546107&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)10646-3

DO - 10.1016/S0040-4039(97)10646-3

M3 - Article

VL - 39

SP - 881

EP - 884

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -