Total Synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Sep 26

PMID 18816134

Citations 9

Authors

Panduka B Koswatta

Rasapalli Sivappa

H V Rasika Dias

Carl J Lovely

Affiliations

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Abstract

The first total synthesis of the Leucetta alkaloid calcaridine A is described based on a biosynthetic postulate. Application of an oxidative rearrangement of a 4,5-disubstituted imidazole leads to the formation of both calcaridine A and epi-calcaridine A. An X-ray crystal structure determination on the latter has allowed the assignment of the relative configuration of the epimeric natural product and calcaridine A by extrapolation.

Citing Articles

Investigation of Dearomatizing Spirocyclizations and Spirocycle Functionalization En Route to Spirocalcaridines A and B-Some Trials and Tribulations.

Singh R, Gout D, Mao J, Kroll P, Lovely C Molecules. 2025; 30(5).

PMID: 40076366 PMC: 11902021. DOI: 10.3390/molecules30051143.

The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products.

Keel K, Tepe J Org Chem Front. 2021; 7(20):3284-3311.

PMID: 33796321 PMC: 8009324. DOI: 10.1039/d0qo00764a.

Total synthesis and cytotoxicity of Leucetta alkaloids.

Koswatta P, Kasiri S, Das J, Bhan A, Lima H, Garcia-Barboza B Bioorg Med Chem. 2017; 25(5):1608-1621.

PMID: 28159485 PMC: 5596918. DOI: 10.1016/j.bmc.2017.01.024.

Studies Towards the -derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.

Koswatta P, Das J, Yousufuddin M, Lovely C European J Org Chem. 2015; 2015(12):2603-2613.

PMID: 26257576 PMC: 4524666. DOI: 10.1002/ejoc.201403650.

Total syntheses of kealiinines A-C.

Das J, Koswatta P, Jones J, Yousufuddin M, Lovely C Org Lett. 2012; 14(24):6210-3.

PMID: 23215346 PMC: 3876472. DOI: 10.1021/ol302958e.

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