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Unified syntheses of cavicularin and riccardin C: addressing the synthesis of an arene adopting a boat configuration

Unified syntheses of cavicularin and riccardin C: addressing the synthesis of an arene adopting a boat configuration
Unified syntheses of cavicularin and riccardin C: addressing the synthesis of an arene adopting a boat configuration
Concise syntheses of the natural products cavicularin (ten steps) and riccardin C (seven steps) are reported. Key features of the new synthetic route are a convergent strategy to assemble acyclic precursors and a sequence of regioselective reduction and halogenation steps to facilitate Wittig macrocyclisation and transannular ring contraction reactions.
0947-6539
10906-10915
Kostiuk, S.L.
e225fe34-eb13-4d1c-9000-917d6f9b164a
Woodcock, T
e3994e66-f0a5-4f05-82d6-778fcc2a017a
Dudin, L.F.
0d989410-9412-4e38-841b-91d34ad569aa
Howes, P.D.
7d03339f-73d9-4caf-b8c4-4a8f09abd247
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Kostiuk, S.L.
e225fe34-eb13-4d1c-9000-917d6f9b164a
Woodcock, T
e3994e66-f0a5-4f05-82d6-778fcc2a017a
Dudin, L.F.
0d989410-9412-4e38-841b-91d34ad569aa
Howes, P.D.
7d03339f-73d9-4caf-b8c4-4a8f09abd247
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b

Kostiuk, S.L., Woodcock, T, Dudin, L.F., Howes, P.D. and Harrowven, David C. (2011) Unified syntheses of cavicularin and riccardin C: addressing the synthesis of an arene adopting a boat configuration. Chemistry - A European Journal, 17 (39), 10906-10915. (doi:10.1002/chem.201101550).

Record type: Article

Abstract

Concise syntheses of the natural products cavicularin (ten steps) and riccardin C (seven steps) are reported. Key features of the new synthetic route are a convergent strategy to assemble acyclic precursors and a sequence of regioselective reduction and halogenation steps to facilitate Wittig macrocyclisation and transannular ring contraction reactions.

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Published date: 18 August 2011
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Organisations: Chemistry
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Identifiers

Local EPrints ID: 195319
URI: http://eprints.soton.ac.uk/id/eprint/195319
DOI: doi:10.1002/chem.201101550
ISSN: 0947-6539
PURE UUID: 6d1208b7-b5ac-4a62-8b4c-de996da95639
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 18 Aug 2011 10:53
Last modified: 15 Mar 2024 02:47

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Contributors

Author: S.L. Kostiuk
Author: T Woodcock
Author: L.F. Dudin
Author: P.D. Howes
Author: David C. Harrowven ORCID iD

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