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ChemInform Abstract: Double Diastereoselection in Intramolecular Photocycloadditions: A Radical Rearrangement Approach to the Total Synthesis of the Spirovetivane Phytoalexin (.+-.)-Lubiminol.

✍ Scribed by M. T. CRIMMINS; Z. WANG; L. A. MCKERLIE

Publisher: John Wiley and Sons
Year: 2010
Weight: 41 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199827305

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✦ Synopsis

Double Diastereoselection in Intramolecular Photocycloadditions:

A Radical Rearrangement Approach to the Total Synthesis of the Spirovetivane Phytoalexin (±)-Lubiminol.

-Key steps in the synthesis of the title compound (XIII) are a conjugate addition-cyclization reaction to prepare compound (III), a highly diastereoselective intramolecular photocycloaddition and the formation of the spirodecane skeleton via a radical fragmentation-rearrangement reaction.

-(CRIMMINS, M. T.;

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Rearrangement of Cyclobutyl Carbinyl Radicals: Total Synthesis of the Spirovetivane Phytoalexin (±)-Lubiminol. -The total synthesis of title compound (VI) relies on the intramolecular photolytic (2 + 2) cycloaddition of the key intermediate (I). The stereoselectively resulting photoadduct (II) is t