Stereoselective Approach to the Racemic Oxatetracyclic Core of Platensimycin

Stereoselective Approach to the Racemic Oxatetracyclic Core of Platensimycin

A highly stereoselective synthesis of the racemic oxatetracyclic core of platensimycin has been accomplished from a known bicyclic epoxy lactone by an 11-step sequence that involves a Diels–Alder cyclcoaddition to construct its cis-decalenone structural motif with complete regio- and stereoselectivi...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 78; no. 6; pp. 2798 - 2801
Main Authors: Horii, Sakuya, Torihata, Munefumi, Nagasawa, Tomohiro, Kuwahara, Shigefumi
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-03-2013
Subjects:
Adamantane - chemical synthesis
Adamantane - chemistry
Aminobenzoates - chemical synthesis
Aminobenzoates - chemistry
Anilides - chemical synthesis
Anilides - chemistry
Cyclization
Cycloaddition Reaction
Molecular Structure
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Stereoisomerism
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Summary:A highly stereoselective synthesis of the racemic oxatetracyclic core of platensimycin has been accomplished from a known bicyclic epoxy lactone by an 11-step sequence that involves a Diels–Alder cyclcoaddition to construct its cis-decalenone structural motif with complete regio- and stereoselectivity and a ring-closing metathesis to establish its whole carbon framework.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302813y