The first synthesis of kaitocephalin based on the structure revision

A total synthesis of kaitocephalin (2), a glutamate receptor antagonist, was accomplished employing a novel stereoselective C C bond forming reaction of a nitrone (8) and a halide (11) with zinc in aqueous solvent under sonication as a key step. The absolute configuration of kaitocephalin was confir...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 5; pp. 861 - 864
Main Authors Watanabe, H, Okue, M, Kobayashi, H, Kitahara, T
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 28.01.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NMDA antagonist
UNSATURATED CARBONYL-COMPOUNDS
ULTRASOUND
ACIDS
ALPHA
kaitocephalin
total synthesis
AMPA KA antagonist
CONJUGATE ADDITIONS
DERIVATIVES
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Summary:A total synthesis of kaitocephalin (2), a glutamate receptor antagonist, was accomplished employing a novel stereoselective C C bond forming reaction of a nitrone (8) and a halide (11) with zinc in aqueous solvent under sonication as a key step. The absolute configuration of kaitocephalin was confirmed to be 2R.3S.4R,7R,9S. (C) 2002 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(01)02255-9