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image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao
ChemInform
Article . 2005 . Peer-reviewed
License: Wiley Online Library User Agreement
Data sources: Crossref
The Journal of Organic Chemistry
Article . 2004 . Peer-reviewed
Data sources: Crossref
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Asymmetric Total Syntheses of (+)‐Mycoepoxydiene (IV) and Related Natural Product (‐)‐1893A (V): Application of One‐Pot Ring‐Opening/Cross/Ring‐Closing Metathesis to Construct Their 9‐Oxabicyclo[4.2.1]nona‐2,4‐diene Skeleton.

Authors: Ken-ichi, Takao; Hiroyuki, Yasui; Shun, Yamamoto; Daisuke, Sasaki; Soujiro, Kawasaki; Gohshi, Watanabe; Kin-ichi, Tadano;

Asymmetric Total Syntheses of (+)‐Mycoepoxydiene (IV) and Related Natural Product (‐)‐1893A (V): Application of One‐Pot Ring‐Opening/Cross/Ring‐Closing Metathesis to Construct Their 9‐Oxabicyclo[4.2.1]nona‐2,4‐diene Skeleton.

Abstract

The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2-ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.

Related Organizations
Keywords

Bridged-Ring Compounds, Pyrones, Molecular Conformation, Cycloparaffins

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Powered by OpenAIRE graph
citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
65
Top 10%
Top 10%
Top 10%