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Toward the total synthesis of lophotoxin - New methodologies and synthetic strategies

Wipf, P and Grenon, M (2006) Toward the total synthesis of lophotoxin - New methodologies and synthetic strategies. Canadian Journal of Chemistry, 84 (10). 1226 - 1241. ISSN 0008-4042

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Abstract

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal- catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation. © 2006 NRC.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Grenon, M
Date: 1 October 2006
Date Type: Publication
Journal or Publication Title: Canadian Journal of Chemistry
Volume: 84
Number: 10
Page Range: 1226 - 1241
DOI or Unique Handle: 10.1139/v06-073
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0008-4042
Date Deposited: 23 Sep 2014 14:49
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/22504

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