A concise diastereoselective approach to (+)-dexoxadrol, (-)-epidexoxadrol, (-)-conhydrine and (+)-lentiginosine from (-)-pipecolinic acid

作者：Bhat Chinmay; Tilve Santosh G^*

来源：Tetrahedron, 2013, 69(51): 10876-10883.

DOI：10.1016/j.tet.2013.10.082

• Piperidines
• Sharpless dihydroxylation
• Wittig reaction
• Alkaloids

A new diastereoselective pathway for the total synthesis of (+)-dexoxadrol, first asymmetric synthesis of (-)-epi-dexoxadrol and formal synthesis of conhydrine and (+)-lentiginosine is presented using commercially available (-)-pipecolinic acid. The key reactions utilized are Sharpless asymmetric dihydroxylation and Wittig reaction. The paper further describes the study of effect of protecting groups on dihydroxylation of a terminal olefin in piperidine ring system.

• 出版日期2013-12-23