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Synfacts 2006(3): 0285-0285  
DOI: 10.1055/s-2006-931999
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of Callipeltin D

Contributor(s): Yasuhiro Uozumi, Ray Kawade, Toshimasa Suzuka
D. C. Cranfill, Á. I. Morales-Ramos, M. A. Lipton*
Purdue University, West Lafayette, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

The efficient solid-phase synthesis of callipeltin D (4) was achieved (7 steps, 35% overall yield) by the standard Fmoc method where (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid was used as an AGDHE unit. The configuration of AGDHE in callipeltin D was confirmed by comparison of the NMR spectra of the synthesized compound 4 with those of the natural callipeltin D. Thus, the configuration of callipeltin D was completely verified [d-allothreonine, d-alanine, (2R,3R,4S)-AGDHE, (2S,3S,4R)-3,4-dimethylglutamine (DiMeGln), and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid (TMHEA)].