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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 17
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Articles

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

Rachana PandeySchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; View further author information
,
Anju GehlawatSchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; View further author information
,
Ranjana PrakashSchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; Correspondence[email protected]
View further author information
&
Satyendra Kumar PandeySchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; ;Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, IndiaCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0001-7839-567XView further author information
ORCID Icon
Pages 2280-2287 | Received 14 May 2018, Published online: 10 Aug 2018
 
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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

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.

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