Enantioselective total syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H

Abstract

An efficient enantioselective approach to the syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H is presented, starting from n-decanol. The synthesis features Sharpless asymmetric dihydroxylation (AD), regioselective epoxide formation/opening and α-tosylation as key steps.

Graphical Abstract

Keywords:

• 2-amino-3-alkanols
• clavaminols
• cytotoxic
• Sharpless AD
• regioselective

Acknowledgments

R. Pandey thanks Thapar Institute of Engineering and Technology for the research associateship and A.G. thanks UGC, New Delhi for research fellowship.

Additional information

Funding

The authors (R.P. and S.K.P.) acknowledge the research grant No. 02(0309)/17/EMR-II facilitated by the CSIR (Council for Scientific and Industrial Research), New Delhi, India for the carrying out the study.