Toward the synthesis of macrolide aspergillide D

Abstract

Stereoselective synthesis of 16-membered macrocyclic core of marine natural product, Aspergillide D is described using linear strategy. The salient features of this synthetic study include the Sharpless asymmetric kinetic resolution followed by regioselective ring-opening reaction of corresponding epoxide to establish the stereo centers and ring-closing metathesis (RCM) by Grubbs'-II catalyst for the construction of macrocyclic ring.

Graphical Abstract

Keywords:

• Macrolide
• natural product
• regioselective ring-opening reaction
• ring-closing metathesis (RCM)
• sharpless kinetic resolution

Acknowledgments

KSR thank UGC, India for the award of fellowship. All the authors thank Council of Scientific and Industrial Research (CSIR), New Delhi, India and CSIR-Indian Institute of Chemical Technology (IICT) for financial support.

IICT Communication No: IICT/Pubs./2019/273.