Toward aflatoxin B2: an unexpected additive effect in a Dötz benzannulation reaction

Stephen A. Eastham; John Herbert; Steven P. Ingham; Peter Quayle; Matthew Wolfendale

doi:10.1016/j.tetlet.2006.07.041

Toward aflatoxin B2: an unexpected additive effect in a Dötz benzannulation reaction

Stephen A. Eastham
, John Herbert
, Steven P. Ingham
, Peter Quayle
, Matthew Wolfendale

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

Abstract

The addition of tolane to an intermolecular Dötz reaction has a profound effect upon the product distribution of the reaction such that cyclopentannulation becomes a major pathway rather than benzannulation. In addition the incorporation of an electron-rich acetylene into the cyclopentannulated product proceeds in a contra-steric fashion, a set of results which has been rationalised in terms of the reversible formation of intermediate π-complexes at the branch point of the benzannulation sequence. © 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6627-6633
Number of pages	6
Journal	Tetrahedron Letters
Volume	47
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.041
Publication status	Published - 11 Sept 2006

Keywords

Allochemical
Benzannulation
Carbene
Chromium
Dötz
Xenochemical

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10.1016/j.tetlet.2006.07.041

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@article{d1f2c11ed35047efa6675632f6f797f0,

title = "Toward aflatoxin B2: an unexpected additive effect in a D{\"o}tz benzannulation reaction",

abstract = "The addition of tolane to an intermolecular D{\"o}tz reaction has a profound effect upon the product distribution of the reaction such that cyclopentannulation becomes a major pathway rather than benzannulation. In addition the incorporation of an electron-rich acetylene into the cyclopentannulated product proceeds in a contra-steric fashion, a set of results which has been rationalised in terms of the reversible formation of intermediate π-complexes at the branch point of the benzannulation sequence. {\textcopyright} 2006 Elsevier Ltd. All rights reserved.",

keywords = "Allochemical, Benzannulation, Carbene, Chromium, D{\"o}tz, Xenochemical",

author = "Eastham, \{Stephen A.\} and John Herbert and Ingham, \{Steven P.\} and Peter Quayle and Matthew Wolfendale",

year = "2006",

month = sep,

day = "11",

doi = "10.1016/j.tetlet.2006.07.041",

language = "English",

volume = "47",

pages = "6627--6633",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Toward aflatoxin B2: an unexpected additive effect in a Dötz benzannulation reaction

AU - Eastham, Stephen A.

AU - Herbert, John

AU - Ingham, Steven P.

AU - Quayle, Peter

AU - Wolfendale, Matthew

PY - 2006/9/11

Y1 - 2006/9/11

N2 - The addition of tolane to an intermolecular Dötz reaction has a profound effect upon the product distribution of the reaction such that cyclopentannulation becomes a major pathway rather than benzannulation. In addition the incorporation of an electron-rich acetylene into the cyclopentannulated product proceeds in a contra-steric fashion, a set of results which has been rationalised in terms of the reversible formation of intermediate π-complexes at the branch point of the benzannulation sequence. © 2006 Elsevier Ltd. All rights reserved.

AB - The addition of tolane to an intermolecular Dötz reaction has a profound effect upon the product distribution of the reaction such that cyclopentannulation becomes a major pathway rather than benzannulation. In addition the incorporation of an electron-rich acetylene into the cyclopentannulated product proceeds in a contra-steric fashion, a set of results which has been rationalised in terms of the reversible formation of intermediate π-complexes at the branch point of the benzannulation sequence. © 2006 Elsevier Ltd. All rights reserved.

KW - Allochemical

KW - Benzannulation

KW - Carbene

KW - Chromium

KW - Dötz

KW - Xenochemical

U2 - 10.1016/j.tetlet.2006.07.041

DO - 10.1016/j.tetlet.2006.07.041

M3 - Article

SN - 1873-3581

VL - 47

SP - 6627

EP - 6633

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Toward aflatoxin B2: an unexpected additive effect in a Dötz benzannulation reaction

Abstract

Keywords

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