Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation.

Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Research Abstract Details 

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Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Abstract Text:

William D Shipe,Erik J Sorensen,

The evolution of a convergent strategy that led to efficient, enantioselective syntheses of both natural (+)- and unnatural (-)-guanacastepene E and formal total syntheses of (+)- and (-)-guanacastepene A is described. A union of five- and six-membered ring intermediates by an efficient pi-allyl Stille cross-coupling reaction was followed by an intramolecular enone-olefin [2 + 2] photocycloaddition and a stereoelectronically controlled, reductive fragmentation of the resulting cyclobutyl ketone. The latter two transformations enabled controlled formation of the C-11 quaternary stereocenter and the central seven-membered ring of the guanacastepenes. An enantiospecific synthesis of the functionalized five-membered ring vinyl stannane from the monoterpene R-(-)-carvone featuring a carbon-carbon bond forming ring contraction was also developed.

Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Publishing Authors By Initials

WD Shipe,EJ Sorensen,

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

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Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of the American Chemical Society

VOLUME: 128

Page Numbers: 7025-35

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 31

MONTH: May

YEAR: 2006

Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Keywords Mesh Terms:

KEYWORDS: Stereoisomerism

MESH TERMS: chemistry

Chemical & Substance for Abstract: Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation. Information

Substance Name: guanacastepene E

Registry Number: 0

Grant and Affiliation Information for Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation.

AFFILIATION: Frick Chemical Laboratory, Princeton University, Princeton, NJ 08544-1009, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM 065483

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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