Total synthesis of Sumalactone A

Abstract

A simple and efficient stereoselective synthesis of 10-membered Benzannulated macrolactone, Sumalactone A has been accomplished from inexpensive and commercially available starting materials. This convergent synthesis utilizes Vilsmeier-Haack formylation, Jacobsen hydrolytic kinetic resolution, esterification under Yamaguchi conditions and ring-closing metathesis as key steps.

Graphical Abstract

Keywords:

• Benzannulated macrolactones
• esterification under Yamaguchi conditions
• Jacobsen hydrolytic kinetic resolution
• sumalactones
• Vilsmeier-Haack formylation

Acknowledgments

We would like to express our gratitude and thanks to Department of Chemistry, Koneru Lakshmaiah University, Guntur for constant encouragement and providing basic research facility.

Supporting information

Full experimental details, spectral data of the products, ¹H NMR and ¹³C NMR of all the new compounds can be found via the Supplementary Content section of this article’s Web page.