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Issue 22, 2019
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Total synthesis and stereochemical revision of relgro and 10′-oxorelgro

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Abstract

The first asymmetric total synthesis and stereochemical assignments of 10-membered macrolactones relgro and 10′-oxorelgro are disclosed. To this end, palladium-catalyzed Stille coupling, the Mitsunobu reaction, ring-closing metathesis, EDCI promoted coupling and the Jacobsen hydrolytic kinetic resolution are used as key steps. The total synthesis followed by thorough evaluation of the optical rotation and CD spectral data led to the revision of the absolute configuration at C-6′ for both relgro and 10′-oxorelgro. Moreover, the 1H as well as 13C NMR data are reported for the first time for relgro.

Graphical abstract: Total synthesis and stereochemical revision of relgro and 10′-oxorelgro

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Publication details

The article was received on 11 Apr 2019, accepted on 15 May 2019 and first published on 16 May 2019


Article type: Paper
DOI: 10.1039/C9OB00838A
Org. Biomol. Chem., 2019,17, 5601-5614

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    Total synthesis and stereochemical revision of relgro and 10′-oxorelgro

    J. Gaddam, G. S. Reddy, K. Marumudi, A. C. Kunwar, J. S. Yadav and D. K. Mohapatra, Org. Biomol. Chem., 2019, 17, 5601
    DOI: 10.1039/C9OB00838A

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