Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A

Synthesis of medium- and large-sized cyclic amines using alkylation with 2-nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been full...

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 32; pp. 6267 - 6276
Main Authors Kan, Toshiyuki, Fujiwara, Akiko, Kobayashi, Hideki, Fukuyama, Tohru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.08.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
cyclization
lipogrammistin-A
Mitsunobu conditions
Physical Sciences
Science & Technology
lipogrammistin-A
cyclization
Mitsunobu conditions
ROUTE
8-MEMBERED RINGS
POLYAMINE TOXIN HO-416B
CYCLIZATIONS
LIPOPHILIC ICHTHYOTOXIN
HETEROCYCLES
NITROGEN
SECONDARY-AMINES
METATHESIS
CYCLIC AMINES
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Summary:Synthesis of medium- and large-sized cyclic amines using alkylation with 2-nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been fully demonstrated in the total synthesis of lipogrammistin-A ( 9 ), an 18-membered cyclic polyamine. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00626-9