Total synthesis of (-)-dysiherbaine [4]

Journal of the American Chemical Society

Volumn 122, Issue 21, 2000, Pages 5216-5217

  Masaki, Hidekazu ^a   Maeyama, Junji ^a   Kamada, Kazuko ^a   Esumi, Tomoyuki ^a   Iwabuchi, Yoshiharu ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NEUROTOXIN;

CHEMICAL STRUCTURE; LETTER; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; TOXIN SYNTHESIS;

EID: 0034738041     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000817s     Document Type: Letter

References (32)

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27. A 1:2 E/Z-mixture of the corresponding trisubstituted alkenyl triflates was also obtained in ∼11% yield.
28. Since methyl 2-(methoxycarbonylamino)acrylate was also formed under these conditions, the use of 3∼5 equiv of N-methoxycarbonyl-β-iodoalanine was required for the sufficient production of the organozinc reagent.
29. 2 resulted in formation of the corresponding six-membered cyclic carbamate rather than the desired cyclization.
30. The CSA catalyzed cyclization provided a 2:3 mixture of 19 and its C4-epimer in 51% yield, and the PPTS catalyzed cyclization gave the C4-epimer of 19 exclusively in 52% yield after methanolysis.
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32. -2 M DCl) of synthetic dysiherbaine was found to be completely identical with that of natural specimen.