Synthesis of Oximinotyrosine-Derived
Marine Natural Products

Fabia Hentschel; Thomas Lindel

doi:10.1055/s-0029-1218615

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Synthesis 2010(2): 181-204
DOI: 10.1055/s-0029-1218615

REVIEW

Synthesis of Oximinotyrosine-Derived Marine Natural Products

Fabia Hentschel, Thomas Lindel*
Institute of Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
Fax: +49(531)3917744; e-Mail: th.lindel@tu-bs.de;

Further Information

Publication History

Received 22 August 2009
Publication Date:
16 December 2009 (online)

Abstract
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Abstract

This review article gives a detailed account on the synthesis of oximinotyrosine-derived marine natural products from sponges of the order Verongida. Oxidation of the amino group of the underlying bromotyrosine building block to the oxime gives rise to unique chemistry. One of the key features of the peptide-like bromotyrosine compounds is their ability to undergo cyclization to spiroisoxazolines and to form diaryl ether linkages.

1 Introduction

2 Open-Chain α-Oximinoamides

2.1 Psammaplin A

2.2 Spermatinamine, Purealidin, Verongamine

2.3 Psammaplysenes

3 Macrocyclic α-Oximinoamides

3.1 Bastadins

3.2 Bastadin Models

4 Spirocyclized α-Oximinoamides

4.1 Aerothionin

4.2 Calafianin

4.3 Purealin A

4.4 Psammaplysin

5 Aeroplysinin-1

6 Summary and Challenges

Key words

marine natural products - bromotyrosine - spirocyclization - diaryl ether - oxime

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