Selective deoxygenation of allylic alcohol: stereocontrolled synthesis of lavandulol.

Hee Jin Kim, Liang Su, Heejung Jung, Sangho Koo

Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, Korea.

Organic letters 2011 May 20

filter terms:

Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl(2)-catalyzed reduction with LiBHEt(3). (+)-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.

Citation

Hee Jin Kim, Liang Su, Heejung Jung, Sangho Koo. Selective deoxygenation of allylic alcohol: stereocontrolled synthesis of lavandulol. Organic letters. 2011 May 20;13(10):2682-5