Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

Robin G. Pritchard; Helen M. Sheldrake; Isobel Z. Taylor; Timothy W. Wallace

doi:10.1016/j.tetlet.2008.04.114

Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

Robin G. Pritchard, Helen M. Sheldrake, Isobel Z. Taylor, Timothy W. Wallace

Research output: Contribution to journal › Article › peer-review

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Abstract

The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene-phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions. © 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4156-4159
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.114
Publication status	Published - 23 Jun 2008

Keywords

α-Bromoketone
6-endo-Trig
Benzo[a]xanthene
Lauroyl peroxide
Merosesquiterpene
Puupehenone
Radical cyclisation
Sesquiterpene-phenol

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10.1016/j.tetlet.2008.04.114

POST-PEER-REVIEW-PUBLISHERS.PDFFinal published version, 272 KB

CCDC 679032: Experimental Crystal Structure Determination
Pritchard, R. (Contributor), Sheldrake, H. M. (Contributor), Taylor, I. Z. (Contributor) & Wallace, T. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2008
DOI: 10.5517/ccqsl8b, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqsl8b&sid=DataCite
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Cite this

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title = "Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones",

abstract = "The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene-phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

keywords = "α-Bromoketone, 6-endo-Trig, Benzo[a]xanthene, Lauroyl peroxide, Merosesquiterpene, Puupehenone, Radical cyclisation, Sesquiterpene-phenol",

author = "Pritchard, {Robin G.} and Sheldrake, {Helen M.} and Taylor, {Isobel Z.} and Wallace, {Timothy W.}",

year = "2008",

month = jun,

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doi = "10.1016/j.tetlet.2008.04.114",

language = "English",

volume = "49",

pages = "4156--4159",

journal = "Tetrahedron Letters",

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publisher = "Elsevier BV",

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Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones. / Pritchard, Robin G.; Sheldrake, Helen M.; Taylor, Isobel Z. et al.

In: Tetrahedron Letters, Vol. 49, No. 26, 23.06.2008, p. 4156-4159.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

AU - Pritchard, Robin G.

AU - Sheldrake, Helen M.

AU - Taylor, Isobel Z.

AU - Wallace, Timothy W.

PY - 2008/6/23

Y1 - 2008/6/23

N2 - The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene-phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions. © 2008 Elsevier Ltd. All rights reserved.

AB - The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene-phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions. © 2008 Elsevier Ltd. All rights reserved.

KW - α-Bromoketone

KW - 6-endo-Trig

KW - Benzo[a]xanthene

KW - Lauroyl peroxide

KW - Merosesquiterpene

KW - Puupehenone

KW - Radical cyclisation

KW - Sesquiterpene-phenol

U2 - 10.1016/j.tetlet.2008.04.114

DO - 10.1016/j.tetlet.2008.04.114

M3 - Article

VL - 49

SP - 4156

EP - 4159

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -

Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones

Abstract

Keywords

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Datasets

CCDC 679032: Experimental Crystal Structure Determination

Cite this