Total Syntheses of the Structures Assigned to the Marine Natural Products Orthoscuticellines A-E

Date

2022-08-29

Authors

Yi, Liangguang
He, Yu-Tao
Tan, Shen
White, Lorenzo V.
Lan, Ping
Gardiner, Michael G.
Pei, Zhipeng
Coote, Michelle L.
Banwell, Martin G.

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

The readily prepared and vinylated β-carboline 11 has been converted over one or two steps into compounds 1-5, the structures assigned to the recently reported marine natural products orthoscuticellines A-E. The spectral data recorded on the synthetically derived compounds are fully consistent with the assigned structures and, on making allowances for variations in the pH of the medium in which the spectra of the natural products were recorded, it is concluded that the structures assigned to orthoscuticellines A-E are most likely correct. Certainly, the calculated 13C NMR spectra of the α-, γ-, and δ-carboline isomers of compounds 1-5 suggest that orthoscuticellines A-E do incorporate the assigned β-carboline core.

Description

Keywords

carbolines, isomerism, magnetic resonance spectroscopy, molecular structure, biological products

Citation

Source

The Journal of organic chemistry

Type

Journal article

Book Title

Entity type

Access Statement

Open Access

License Rights

DOI

10.1021/acs.joc.2c01477

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