Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic.

Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Research Abstract Details 

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Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Abstract Text:

Amos B Smith,Vladimir Simov,

[Structure: see text] The total synthesis of the marine diolide (-)-clavosolide A has been achieved in 17 steps (longest linear sequence) from commercially available crotonaldehyde exploiting the Petasis-Ferrier union/rearrangement tactic to construct the requisite aglycon monomer. A one-pot esterification/lactonization employing the Yamaguchi protocol, followed by bis-glycosidation, furnished (-)-clavosolide A.

Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Publishing Authors By Initials

AB Smith,V Simov,

For similar natural sciences: chemistry: chemistry, organic: isomerism: stereoisomerism research abstracts see: natural sciences: chemistry: chemistry, organic: isomerism: stereoisomerism research

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Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Organic letters

VOLUME: 8

Page Numbers: 3315-8

Journal Abbreviation: Org. Lett.

ISSN: 1523-7060

DAY: 20

MONTH: Jul

YEAR: 2006

Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Information

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LANGUAGE: eng

NlmUniqueID: 100890393

Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Keywords Mesh Terms:

KEYWORDS: Stereoisomerism

MESH TERMS: chemistry

Chemical & Substance for Abstract: Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic. Information

Substance Name: clavosolide A

Registry Number: 0

Grant and Affiliation Information for Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic.

AFFILIATION: Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu

Country: United States

AGENCY: United States NIGMS

GRANT: GM-29028

ACRONYM: GM

MEDLINETA: Org Lett

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