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CSIRO Publishing, Australian Journal of Chemistry, 5(63), p. 797, 2010

DOI: 10.1071/ch09643

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Synthesis of Cyclogossine B Using a Traceless Pseudoproline Turn-Inducer

Journal article published in 2010 by Michelle S. Y. Wong, Katrina A. Jolliffe ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The first synthesis of the cyclic octapeptide, cyclogossine B, has been achieved, confirming the reported structure of this natural product. Cyclization of a linear precursor containing a cysteine-derived thiazolidine as a traceless turn-inducer occurred in significantly higher yields than cyclization of the analogous alanine-containing precursor under identical conditions. Deprotection of the thiazolidine followed by desulfurization provided cyclogossine B in good overall yield, indicating that cysteine-derived pseudoprolines can be effectively used as traceless turn-inducers to facilitate the cyclization of small peptides.