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Synthesis 2011(24): 4033-4036  
DOI: 10.1055/s-0031-1289594
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Straightforward Approach to Protected (S)-Dolaphenine (Doe), the Unusual Amino Acid Component of Dolastatin 10

Jens L. Burkhart, Uli Kazmaier*
Institut für Organische Chemie, Universitaet des Saarlandes, 66123 Saarbruecken, Germany
Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;
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Publikationsverlauf

Received 16 September 2011
Publikationsdatum:
07. November 2011 (online)

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Abstract

A short, four-step synthesis of Boc-protected (S)-dolaphenine is described, starting from protected phenylalanyl glycine. The key step is the cyclization of an endothiodipeptide to give a thiazolyl­ triflate, which can be subjected to a palladium-catalyzed reduction with formic acid.

Key words

dolaphenine - dolastatin - endothiopeptides - peptides - thiazoles - triflates

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