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

I. Wayan Mudianta; Peter L. Katavic; Lynette K. Lambert; Patricia Y. Hayes; Martin G. Banwell; Murray H.G. Munro; Paul V. Bernhardt; Mary J. Garson

doi:10.1016/j.tet.2010.01.068

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

I. Wayan Mudianta
, Peter L. Katavic
, Lynette K. Lambert
, Patricia Y. Hayes
, Martin G. Banwell
, Murray H.G. Munro
, Paul V. Bernhardt
, Mary J. Garson^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2752-2760
Number of pages	9
Journal	Tetrahedron
Volume	66
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2010.01.068
Publication status	Published - 3 Apr 2010

Access to Document

10.1016/j.tet.2010.01.068

Cite this

@article{5992045bbb7b4d59ad3f3d9f7f080a67,

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

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.",

keywords = "3-Alkylpiperidine, Absolute configuration, Biosynthesis, Halichondria, N-Oxide, NMR, Sponge, X-ray analysis",

author = "Mudianta, \{I. Wayan\} and Katavic, \{Peter L.\} and Lambert, \{Lynette K.\} and Hayes, \{Patricia Y.\} and Banwell, \{Martin G.\} and Munro, \{Murray H.G.\} and Bernhardt, \{Paul V.\} and Garson, \{Mary J.\}",

year = "2010",

month = apr,

day = "3",

doi = "10.1016/j.tet.2010.01.068",

language = "English",

volume = "66",

pages = "2752--2760",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "14",

}

TY - JOUR

T1 - Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria

AU - Mudianta, I. Wayan

AU - Katavic, Peter L.

AU - Lambert, Lynette K.

AU - Hayes, Patricia Y.

AU - Banwell, Martin G.

AU - Munro, Murray H.G.

AU - Bernhardt, Paul V.

AU - Garson, Mary J.

PY - 2010/4/3

Y1 - 2010/4/3

N2 - 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.

AB - 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.

KW - 3-Alkylpiperidine

KW - Absolute configuration

KW - Biosynthesis

KW - Halichondria

KW - N-Oxide

KW - NMR

KW - Sponge

KW - X-ray analysis

UR - https://www.scopus.com/pages/publications/77649190429

U2 - 10.1016/j.tet.2010.01.068

DO - 10.1016/j.tet.2010.01.068

M3 - Article

SN - 0040-4020

VL - 66

SP - 2752

EP - 2760

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this