Synthesis of Nemorosone via a Difficult Bridgehead Substitution Reaction

Nigel Simpkins; James Taylor; Michael Weller; CJ Hayes

doi:10.1055/s-0029-1219371

Synthesis of Nemorosone via a Difficult Bridgehead Substitution Reaction

Nigel Simpkins, James Taylor, Michael Weller, CJ Hayes

Chemistry

Research output: Contribution to journal › Article

29 Citations (Scopus)

Abstract

The synthesis of nemorosone, a polyprenylated acylphloroglucinol isolated from Clusia rosea, was achieved by means of a bridgehead substitution process, involving initial iodination and subsequent lithium-iodine exchange followed by acylation. The difficulties in the bridgehead substitution are discussed, and a probable explanation proposed, based on molecular modelling.

Original language	English
Pages (from-to)	639-643
Number of pages	5
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-0029-1219371
Publication status	Published - 1 Mar 2010

Keywords

nemorosone
iodine-lithium exchange
bridgehead substitution
B3LYP calculations

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10.1055/s-0029-1219371

Rapid synthesis of complex bioactive alkaloids
Simpkins, N.
Engineering & Physical Science Research Council
1/10/09 → 30/09/12
Project: Research Councils

Cite this

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abstract = "The synthesis of nemorosone, a polyprenylated acylphloroglucinol isolated from Clusia rosea, was achieved by means of a bridgehead substitution process, involving initial iodination and subsequent lithium-iodine exchange followed by acylation. The difficulties in the bridgehead substitution are discussed, and a probable explanation proposed, based on molecular modelling.",

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AU - Weller, Michael

AU - Hayes, CJ

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N2 - The synthesis of nemorosone, a polyprenylated acylphloroglucinol isolated from Clusia rosea, was achieved by means of a bridgehead substitution process, involving initial iodination and subsequent lithium-iodine exchange followed by acylation. The difficulties in the bridgehead substitution are discussed, and a probable explanation proposed, based on molecular modelling.

AB - The synthesis of nemorosone, a polyprenylated acylphloroglucinol isolated from Clusia rosea, was achieved by means of a bridgehead substitution process, involving initial iodination and subsequent lithium-iodine exchange followed by acylation. The difficulties in the bridgehead substitution are discussed, and a probable explanation proposed, based on molecular modelling.

KW - nemorosone

KW - iodine-lithium exchange

KW - bridgehead substitution

KW - B3LYP calculations

U2 - 10.1055/s-0029-1219371

DO - 10.1055/s-0029-1219371

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JO - Synlett

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ER -

Synthesis of Nemorosone via a Difficult Bridgehead Substitution Reaction

Abstract

Keywords

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Projects

Rapid synthesis of complex bioactive alkaloids

Cite this