A new synthetic method for an acromelic acid analog, a potent neuroexcitatory kainoid amino acid, via photoinduced benzyl radical cyclization

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7777-7780

  Itadani, Satoshi ^a   Takai, Shigeyuki ^a   Tanigawa, Chieko ^a   Hashimoto, Kimiko ^b   Shirahama, Haruhisa ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b RIKEN Center for Sustainable Resource Science   (Japan)

Author keywords

Benzyl radical; Kainoid; Photoreaction; Radical cyclization; Salt effect

Indexed keywords

ACROMELIC ACID DERIVATIVE; BENZENE DERIVATIVE; KAINIC ACID RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ARTICLE; CENTRAL NERVOUS SYSTEM; CHEMICAL REACTION; CYCLIZATION; DEPOLARIZATION; DRUG POTENCY; DRUG SYNTHESIS; IRRADIATION; LIGHT; MUSHROOM; NONHUMAN; PHOTOREACTIVITY; PROTON TRANSPORT; REDUCTION; STEREOCHEMISTRY;

EID: 0037152348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01817-8     Document Type: Article

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23. 2 hybridization, which might be disadvantage to adopt the suitable conformation for the cyclization. Accordingly, the amide derivative fell into equilibration between [A] and [D]. The salt added might prevent [D] to [A] by some effects (cf. Ref. ), which promotes further cyclization. In the ether series, the major product had 3,4-trans configuration. This might be attributable to the structure of the radical acceptor, i.e. ester, and also the solvent used, i.e. acetonitrile.
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