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

doi:10.1016/S0040-4039(97)10646-3

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 journal › Article › peer-review

24 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.

Original language	English
Pages (from-to)	881-884
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(97)10646-3
Publication status	Published - 19 Feb 1998
Externally published	Yes

Access to Document

10.1016/S0040-4039(97)10646-3Licence: Unspecified

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 = feb,

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",

}

TY - JOUR

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

T2 - Syntheses of the rotenoid core and related benzoxanthones

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

AN - SCOPUS:0032546107

SN - 0040-4039

VL - 39

SP - 881

EP - 884

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this