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Unified total synthesis of (+)-chinensiolide B and (+)-8-epigrosheimin

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Abstract

An expedient synthetic approach has been developed for the unified total synthesis of (+)-chinensiolide B and (+)-8-epigrosheimin. The point of divergence was provided by the lactone aldehyde 6, in which four contiguous stereocenters were achieved by a stereocontrolled Evans syn-aldol reaction of a R-carvone derived enantiopure aldehyde and chiral N-succinyl-oxazolidinone. The lactone aldehyde 6 was synthesized in multigram quantity in three steps. Highly optimized chemo- and stereoselective reactions and functional group interconversion enabled us to assemble (+)-chinensiolide B and (+)-8-epigrosheimin from 6.

Graphical abstract: Unified total synthesis of (+)-chinensiolide B and (+)-8-epigrosheimin

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Publication details

The article was received on 18 May 2017, accepted on 10 Jul 2017 and first published on 10 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01217A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Unified total synthesis of (+)-chinensiolide B and (+)-8-epigrosheimin

    S. Hajra, S. Acharyya, A. Mandal and R. Maity, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01217A

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