Diyne mediated formal synthesis of (−)-A26771B

Abstract

A formal asymmetric synthesis of (−)-A26771B (1) has been achieved where optically active glycidol and Noyori asymmetric hydrogenation are applied to introduce asymmetric centers. Commercially available 1,7-octadiyne, (R)-glycidol and acetaldehyde are used as the starting materials. The outlined synthetic strategy involves fewer number of synthetic steps, applying simple chemical transformations.

Graphical Abstract

Keywords:

• Epoxide ring opening
• macrolide
• Noyori asymmetric hydrogenation
• octadiyne

Acknowledgments

The authors acknowledge NIT Sikkim for infrastructure support and Dr. Sajal Das (NBU), Mr. Joyanta Mondal, and Mr. Susanta Mandal for constant support.

Additional information

Funding

The Department of Science and Technology, Ministry of Science and Technology, Govt. of India (INSP IRE Faculty Award IFA 12-CH 45) is gratefully acknowledged for financial support.