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Total synthesis of cavicularin and riccardin C: addressing the synthesis of an arene that adopts a boat configuration

Total synthesis of cavicularin and riccardin C: addressing the synthesis of an arene that adopts a boat configuration
Total synthesis of cavicularin and riccardin C: addressing the synthesis of an arene that adopts a boat configuration
A transannular ring contraction induced by the addition of an aryl radical intermediate to a proximal arene facilitated the construction of the highly strained macrocyclic core of cavicularin (1). The precursor, an iodinated derivative of another natural product, riccardin C, was prepared from four commercially available arenes in a highly convergent sequence.
arenes, macrocycles, radical reactions ring, contraction, total synthesisintramolecular radical additions, liverwort, bis(bibenzyls), cyclizations, constituents, vancomycin
1433-7851
3899-3901
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Woodcock, Timothy
b4c00cd0-e2f2-4f4a-8583-b7405de25b2e
Howes, Peter D.
26bf5364-cf38-4981-9218-6d74df1e9529
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Woodcock, Timothy
b4c00cd0-e2f2-4f4a-8583-b7405de25b2e
Howes, Peter D.
26bf5364-cf38-4981-9218-6d74df1e9529

Harrowven, David C., Woodcock, Timothy and Howes, Peter D. (2005) Total synthesis of cavicularin and riccardin C: addressing the synthesis of an arene that adopts a boat configuration. Angewandte Chemie International Edition, 44 (25), 3899-3901. (doi:10.1002/anie.200500466). (PMID:15900530)

Record type: Article

Abstract

A transannular ring contraction induced by the addition of an aryl radical intermediate to a proximal arene facilitated the construction of the highly strained macrocyclic core of cavicularin (1). The precursor, an iodinated derivative of another natural product, riccardin C, was prepared from four commercially available arenes in a highly convergent sequence.

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Published date: 20 June 2005
Keywords: arenes, macrocycles, radical reactions ring, contraction, total synthesisintramolecular radical additions, liverwort, bis(bibenzyls), cyclizations, constituents, vancomycin

Identifiers

Local EPrints ID: 20817
URI: http://eprints.soton.ac.uk/id/eprint/20817
ISSN: 1433-7851
PURE UUID: 37e54c3f-67de-43a9-aa6d-2d93be819b90
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 03 Mar 2006
Last modified: 07 Oct 2020 01:51

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Author: Timothy Woodcock
Author: Peter D. Howes

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