Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C

Brigitte E.A. Burm; Michaël M. Meijler; Jacco Korver; Martin J. Wanner; Gerrit Jan Koomen

doi:10.1016/S0040-4020(98)00306-8

Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C

Brigitte E.A. Burm, Michaël M. Meijler, Jacco Korver, Martin J. Wanner, Gerrit Jan Koomen

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

33 Scopus citations

Abstract

A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.

Original language	English
Pages (from-to)	6135-6146
Number of pages	12
Journal	Tetrahedron
Volume	54
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4020(98)00306-8
State	Published - 28 May 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4020(98)00306-8

Cite this

@article{ac89db273e74462daec9d64286343c10,

title = "Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C",

abstract = "A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.",

author = "Burm, {Brigitte E.A.} and Meijler, {Micha{\"e}l M.} and Jacco Korver and Wanner, {Martin J.} and Koomen, {Gerrit Jan}",

year = "1998",

month = may,

day = "28",

doi = "10.1016/S0040-4020(98)00306-8",

language = "English",

volume = "54",

pages = "6135--6146",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "22",

}

TY - JOUR

T1 - Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C

AU - Burm, Brigitte E.A.

AU - Meijler, Michaël M.

AU - Korver, Jacco

AU - Wanner, Martin J.

AU - Koomen, Gerrit Jan

PY - 1998/5/28

Y1 - 1998/5/28

N2 - A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.

AB - A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.

UR - http://www.scopus.com/inward/record.url?scp=0032575230&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(98)00306-8

DO - 10.1016/S0040-4020(98)00306-8

M3 - Article

AN - SCOPUS:0032575230

SN - 0040-4020

VL - 54

SP - 6135

EP - 6146

JO - Tetrahedron

JF - Tetrahedron

IS - 22

ER -

Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this