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Synthesis of the proposed structure and revision of stereochemistry of kaitocephalin

✍ Scribed by Masayuki Okue; Hiroyuki Kobayashi; Kazuo Shin-ya; Kazuo Furihata; Yoichi Hayakawa; Haruo Seto; Hidenori Watanabe; Takeshi Kitahara

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
77 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A stereoselective total synthesis of the proposed structure of kaitocephalin (1) was accomplished starting from L-proline and D-and L-serines. However, its 1 H NMR spectral data and retention time on HPLC were not identical with those of authentic natural kaitocephalin. The revised stereochemistry of natural kaitocephalin, (2R)-isomer ( 16), was inferred from further experiments employing diastereomers and model compounds.

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