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Total synthesis of (-)-colombiasin A and (-)-elisapterosin B

Total synthesis of (-)-colombiasin A and (-)-elisapterosin B
Total synthesis of (-)-colombiasin A and (-)-elisapterosin B
Intramolecular cycloaddition reactions are central in the total syntheses of colombiasin A (1) and elisapterosin B (2) described, which use (?)-dihydrocarvone as the starting material. A Moore rearrangement of a vinylcyclobutene is used to initiate the cycloaddition.
cycloaddition, diterpenes, marine natural products, rearrangement total synthesis, pseudopterogorgia-elisabethae bayer, colombiasin-a, tetracyclic framework, carbonyl-compounds, olefin formation, stereochemistry, terpenoids, sulfones, strategy
1433-7851
1221-1222
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Pascoe, David D.
15deb860-264b-4bdd-8b73-10fddabdadeb
Demurtas, Daniela
7ca90126-8adf-40cb-96ef-51f7790b348d
Bourne, Heather O.
2808d902-d6c5-4b36-a710-bb6527dfff66
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Pascoe, David D.
15deb860-264b-4bdd-8b73-10fddabdadeb
Demurtas, Daniela
7ca90126-8adf-40cb-96ef-51f7790b348d
Bourne, Heather O.
2808d902-d6c5-4b36-a710-bb6527dfff66

Harrowven, David C., Pascoe, David D., Demurtas, Daniela and Bourne, Heather O. (2005) Total synthesis of (-)-colombiasin A and (-)-elisapterosin B. Angewandte Chemie International Edition, 44 (8), 1221-1222. (doi:10.1002/anie.200462268). (PMID:15696589)

Record type: Article

Abstract

Intramolecular cycloaddition reactions are central in the total syntheses of colombiasin A (1) and elisapterosin B (2) described, which use (?)-dihydrocarvone as the starting material. A Moore rearrangement of a vinylcyclobutene is used to initiate the cycloaddition.

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More information

Published date: 5 February 2005
Keywords: cycloaddition, diterpenes, marine natural products, rearrangement total synthesis, pseudopterogorgia-elisabethae bayer, colombiasin-a, tetracyclic framework, carbonyl-compounds, olefin formation, stereochemistry, terpenoids, sulfones, strategy

Identifiers

Local EPrints ID: 20816
URI: http://eprints.soton.ac.uk/id/eprint/20816
ISSN: 1433-7851
PURE UUID: 544b5a34-0ebb-408b-a9d3-ebbe40d7035c
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 02 Mar 2006
Last modified: 07 Oct 2020 01:51

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Contributors

Author: David D. Pascoe
Author: Daniela Demurtas
Author: Heather O. Bourne

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