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A bioinspired approach for construction of the [7-5-6-5] all-carbon tetracyclic core of logeracemin A

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Abstract

An efficient synthetic approach for the spiro-linked [7-5-6-5] all-carbon tetracyclic core derivatives of logeracemin A, a unique dimeric calyciphylline A-type alkaloid, from the known methyl cyclohept-1-ene carboxylate was described. The synthesis features a bioinspired successive Michael/double aldol/dehydration reaction sequence, which might indicate the possibility of a more efficient alternative biosynthetic pathway of logeracemin A.

Graphical abstract: A bioinspired approach for construction of the [7-5-6-5] all-carbon tetracyclic core of logeracemin A

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Publication details

The article was received on 15 Jan 2019, accepted on 31 Jan 2019 and first published on 02 Feb 2019


Article type: Research Article
DOI: 10.1039/C9QO00062C
Citation: Org. Chem. Front., 2019, Advance Article

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    A bioinspired approach for construction of the [7-5-6-5] all-carbon tetracyclic core of logeracemin A

    L. Gao, B. Cheng, H. Yue, S. Cao, J. Wang and L. Xu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00062C

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