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Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria

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Date

2010

Authors

Mudianta, Wayan
Katavic, Peter L
Lambert, Lynette K
Hayes, Patricia Y
Banwell, Martin
Munro, Murray HG
Bernhardt, Paul
Garson, Mary J

Journal Title

Journal ISSN

Volume Title

Publisher

Elsevier

Abstract

Chemical analysis of an Indonesian sponge sample has provided three new 3-alkylpiperidine alkaloids, tetradehydrohaliclonacyclamine A, its mono-N-oxide derivative, and a 2-epi isomer. The absolute structure of tetradehydrohaliclonacyclamine A has been established by X-ray crystallography from anomalous dispersion effects using Cu radiation, which determined that the absolute configuration is 2S, 3S, 7S, 9S while an HPLC study revealed that the alkaloid is enantiomerically pure.

Description

Keywords

Keywords: alkaloid derivative; alkyl group; copper; piperidine derivative; tetradehydrohaliclonacyclamine a; unclassified drug; article; drug structure; enantiomer; halichondria; high performance liquid chromatography; Indonesia; irradiation; isomer; nonhuman; nucl 3-Alkylpiperidine; Absolute configuration; Biosynthesis; Halichondria; N-Oxide; NMR; Sponge; X-ray analysis

Citation

URI

http://hdl.handle.net/1885/22474

Collections

ANU Research Publications

Source

Tetrahedron

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1016/j.tet.2010.01.068

Restricted until

2037-12-31

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01_Mudianta_Structure_and_absolute_2010.pdf (560.03 KB)

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