Selective Deoxygenation of Allylic Alcohol: Stereocontrolled Synthesis of Lavandulol

Selective Deoxygenation of Allylic Alcohol: Stereocontrolled Synthesis of Lavandulol

Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the P...

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Veröffentlicht in:Organic letters 2011-05, Vol.13 (10), p.2682-2685
Hauptverfasser: Kim, Hee Jin, Su, Liang, Jung, Heejung, Koo, Sangho
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Monoterpenes - chemical synthesis
Monoterpenes - chemistry
Oxidation-Reduction
Palladium - chemistry
Propanols - chemistry
Stereoisomerism
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Zusammenfassung:Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (−)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200779y