Synthesis 2006(15): 2580-2584  
DOI: 10.1055/s-2006-942477
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Total Synthesis of the Marine Natural Product Viscosamine [1]

Christoph Timm, Matthias Köck*
Alfred-Wegener-Institut für Polar- und Meeresforschung in der Helmholtz-Gemeinschaft, Am Handelshafen 12, D-27570 Bremerhaven, Germany
Fax: +49(471)48311425; e-Mail: mkoeck@awi-bremerhaven.de;
Further Information

Publication History

Received 26 January 2006
Publication Date:
11 July 2006 (eFirst)

Abstract

Pyridinium alkaloids are widely distributed in marine sponges of the order Haplosclerida. The cyclic trimeric 3-alkylpyridinium alkaloid viscosamine, from the Arctic sponge Haliclona viscosa, was synthesised through a ten-step synthesis starting from pyridylalcohol in 8% overall yield. Key steps involved the simultaneous activation and deprotection of an open chain precursor, followed by cyclisation under highly dilution conditions. Viscosamine is the first cyclotrimeric 3-alkylpyridinium natural product obtained by total synthesis.

1

Presented at the 4th European Conference on Marine Natural Products, Paris, France, Sept. 12-16, 2005 (Book of abstracts page P82).

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1

Presented at the 4th European Conference on Marine Natural Products, Paris, France, Sept. 12-16, 2005 (Book of abstracts page P82).

10

This peak was not observed again in the new MS measurements since acetic acid was artificially introduced as a trace in the first investigation.