The University of Southampton
University of Southampton Institutional Repository

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.

This record has no associated files available for download.

More information

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

Catalogue record

Date deposited: 03 Mar 2006
Last modified: 16 Mar 2024 02:46

Export record

Altmetrics

Contributors

Author: Timothy Woodcock
Author: Peter D. Howes

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×