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
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
5 February 2005
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), .
(doi:10.1002/anie.200462268).
(PMID:15696589)
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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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
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Date deposited: 02 Mar 2006
Last modified: 16 Mar 2024 02:46
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Author:
David D. Pascoe
Author:
Daniela Demurtas
Author:
Heather O. Bourne
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