Synthesis of the 11-membered ring of the marine alkaloids, madangamines

The first successful attempt at synthesizing the 11-membered ring of madangamine alkaloids is described. The synthesis involves intramolecular N,O-acetalization of a cyclohexanone derivative, cross-coupling reaction with ( Z)-vinylstannane, and intramolecular reductive amination for elaboration of t...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 20; pp. 3489 - 3492
Main Authors Yoshimura, Yuta, Inoue, Junji, Yamazaki, Naoki, Aoyagi, Sakae, Kibayashi, Chihiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.05.2006
Elsevier
Subjects
Alkaloid
Chemistry
Chemistry, Organic
Macrocyclization
Madangamine
N,O-Acetalization
Physical Sciences
Science & Technology
Alkaloid
N,O-Acetalization
Macrocyclization
Madangamine
madangamine
TRICYCLIC CORE
macrocyclization
SPONGE XESTOSPONGIA-INGENS
N,O-acetalization
CATALYST
alkaloid
MICHAEL ADDITION
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Summary:The first successful attempt at synthesizing the 11-membered ring of madangamine alkaloids is described. The synthesis involves intramolecular N,O-acetalization of a cyclohexanone derivative, cross-coupling reaction with ( Z)-vinylstannane, and intramolecular reductive amination for elaboration of the 11-membered macrocycle.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.02.160