A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis.

A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Research Abstract Details 

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A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Abstract Text:

David A Vosburg,Christopher D Vanderwal,Erik J Sorensen,

An efficient biomimetic synthesis of the reported structure of the hexacyclic, cytotoxic secondary metabolite FR182877 is described. The successful route features the synthesis of a 19-membered ring carbocycle using two pi-allyl palladium(II)-mediated C-C bond-forming reactions. This polyunsaturated macrocycle undergoes tandem transannular Diels-Alder reactions that create five rings and seven stereogenic centers in one operation under mild conditions, representing the first double transannular Diels-Alder reaction. The absolute stereochemistry of the natural product is demonstrated to be opposite of that reported previously. Significant quantities of both enantiomers of this microtubule-stabilizing natural product and related structures are now available via this approach.

A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Publishing Authors By Initials

DA Vosburg,CD Vanderwal,EJ Sorensen,

For similar polycyclic compounds research abstracts see: polycyclic compounds research

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A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 124

Page Numbers: 4552-3

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 1

MONTH: May

YEAR: 2002

A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Keywords Mesh Terms:

KEYWORDS: Polycyclic Compounds

MESH TERMS: chemical synthesis

Chemical & Substance for Abstract: A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis. Information

Substance Name: Polycyclic Compounds

Registry Number: 0

Grant and Affiliation Information for A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis.

AFFILIATION: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.

Country: United States

AGENCY: United States NCI

GRANT: CA85526

ACRONYM: CA

MEDLINETA: J Am Chem Soc

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