Tetrahedron 2018-03-10

Diastereoselective approach to trans-5-hydroxy-6-substitutedethanone-2-piperidinones: Scalable syntheses of (+)-febrifugine and (+)-halofuginone

Chen Wang, Yi-Wen Liu, Zhu Zhou, Chang-Mei Si, Xun Sun, Bang-Guo Wei

Index: 10.1016/j.tet.2018.03.022

Full Text: HTML

Abstract

An efficient diastereoselective approach to access trans-5-hydroxy-6-substitutedethanone-2-piperidinones skeleton has been developed through sequential addition-deprotection-cyclization process involving aldimine 6 with substituted acetones. The diastereoselectivity of substitution at C-6 position of 2-piperidinone was controlled by α-siloxyl group and chiral sulfinamide moiety. In addition, the utility of this effective approach is demonstrated by the scalable syntheses of (+)-febrifugine (2) and (+)-halofuginone (4).

Latest Articles:

Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides

2018-04-11

[10.1016/j.tet.2018.03.003]

A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

2018-04-11

[10.1016/j.tet.2018.04.022]

Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin

2018-04-10

[10.1016/j.tet.2018.02.051]

Process design methodology for organometallic chemistry in continuous flow systems

2018-04-07

[10.1016/j.tet.2018.04.020]

Substrate engineering: Effects of different N-protecting groups in the CAL-B-catalysed asymmetric O-acylation of 1-hydroxymethyl-tetrahydro-β-carbolines

2018-04-07

[10.1016/j.tet.2018.04.012]

More Articles...