The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template

Research paper by Karabasappa Mailar, Won Jun Choi

Indexed on: 17 Jun '16Published on: 16 Jun '16Published in: Carbohydrate Research


A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the β-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, β-hydroxyl γ-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate.

Graphical abstract 10.1016/j.carres.2016.06.005.jpg
Figure 10.1016/j.carres.2016.06.005.0.jpg
Figure 10.1016/j.carres.2016.06.005.1.jpg
Figure 10.1016/j.carres.2016.06.005.2.jpg
Figure 10.1016/j.carres.2016.06.005.3.jpg