An approach to cannabinoids by radical cyclisation of 1,7-dienes using diethyl thiophosphite

Mark P. Healy; Andrew F. Parsons; James G. T. Rawlinson

doi:10.1055/s-2008-1032049

An approach to cannabinoids by radical cyclisation of 1,7-dienes using diethyl thiophosphite

Mark P. Healy, Andrew F. Parsons, James G. T. Rawlinson

Chemistry

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

Abstract

Various 1,7-dienes, prepared efficiently in five steps from salicylaldehyde, react with diethyl thiophosphite (in the presence of AIBN) to form substituted chromans, which are potential precursors to cannabinoids. The influence of the substitution of the 1,7-diene on the efficiency of the radical cyclisation is discussed.

Original language	English
Pages (from-to)	329-332
Number of pages	4
Journal	Synlett
Volume	2008
Issue number	3
DOIs	https://doi.org/10.1055/s-2008-1032049
Publication status	Published - 12 Feb 2008

Keywords

addition reactions
cyclisations
ethers
radical reactions
substituent effects
PHOSPHORUS-CENTERED RADICALS
EMMONS-TYPE REACTIONS
PHARMACOPHORIC REQUIREMENTS
STEREOSELECTIVE-SYNTHESIS
ADDITION REACTIONS
SIDE-CHAIN
RECEPTORS
ANALOGS
ETHERS
METHODOLOGY

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10.1055/s-2008-1032049

https://www.thieme-connect.de/DOI/DOI?10.1055/s-2008-1032049

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title = "An approach to cannabinoids by radical cyclisation of 1,7-dienes using diethyl thiophosphite",

abstract = "Various 1,7-dienes, prepared efficiently in five steps from salicylaldehyde, react with diethyl thiophosphite (in the presence of AIBN) to form substituted chromans, which are potential precursors to cannabinoids. The influence of the substitution of the 1,7-diene on the efficiency of the radical cyclisation is discussed.",

keywords = "addition reactions, cyclisations, ethers, radical reactions, substituent effects, PHOSPHORUS-CENTERED RADICALS, EMMONS-TYPE REACTIONS, PHARMACOPHORIC REQUIREMENTS, STEREOSELECTIVE-SYNTHESIS, ADDITION REACTIONS, SIDE-CHAIN, RECEPTORS, ANALOGS, ETHERS, METHODOLOGY",

author = "Healy, {Mark P.} and Parsons, {Andrew F.} and Rawlinson, {James G. T.}",

year = "2008",

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doi = "10.1055/s-2008-1032049",

language = "English",

volume = "2008",

pages = "329--332",

journal = "Synlett",

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T1 - An approach to cannabinoids by radical cyclisation of 1,7-dienes using diethyl thiophosphite

AU - Healy, Mark P.

AU - Parsons, Andrew F.

AU - Rawlinson, James G. T.

PY - 2008/2/12

Y1 - 2008/2/12

N2 - Various 1,7-dienes, prepared efficiently in five steps from salicylaldehyde, react with diethyl thiophosphite (in the presence of AIBN) to form substituted chromans, which are potential precursors to cannabinoids. The influence of the substitution of the 1,7-diene on the efficiency of the radical cyclisation is discussed.

AB - Various 1,7-dienes, prepared efficiently in five steps from salicylaldehyde, react with diethyl thiophosphite (in the presence of AIBN) to form substituted chromans, which are potential precursors to cannabinoids. The influence of the substitution of the 1,7-diene on the efficiency of the radical cyclisation is discussed.

KW - addition reactions

KW - cyclisations

KW - ethers

KW - radical reactions

KW - substituent effects

KW - PHOSPHORUS-CENTERED RADICALS

KW - EMMONS-TYPE REACTIONS

KW - PHARMACOPHORIC REQUIREMENTS

KW - STEREOSELECTIVE-SYNTHESIS

KW - ADDITION REACTIONS

KW - SIDE-CHAIN

KW - RECEPTORS

KW - ANALOGS

KW - ETHERS

KW - METHODOLOGY

UR - http://www.scopus.com/inward/record.url?scp=39749186596&partnerID=8YFLogxK

U2 - 10.1055/s-2008-1032049

DO - 10.1055/s-2008-1032049

M3 - Article

SN - 0936-5214

VL - 2008

SP - 329

EP - 332

JO - Synlett

JF - Synlett

IS - 3

ER -

An approach to cannabinoids by radical cyclisation of 1,7-dienes using diethyl thiophosphite

Abstract

Keywords

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