Total synthesis of haliclamine A, a macrocyclic marine alkaloid related to the key biogenetic intermediate of manzamines

The first total synthesis of haliclamine A ( 1), a macrocyclic marine alkaloid closely related to the key bisdihydropyridine intermediate 3 of the biogenetically unique manzamine family, has been efficiently achieved via stepwise inter- and intramolecular N-alkylations of 3-alkylpyridine derivatives...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 52; pp. 8981 - 8984
Main Authors Morimoto, Yoshiki, Yokoe, Chiho
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.12.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GENUS HALICLONA
BIOMIMETIC APPROACH
MODEL
SPONGE HALICLONA SP
BIOSYNTHESIS
HALICYCLAMINE-A
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Summary:The first total synthesis of haliclamine A ( 1), a macrocyclic marine alkaloid closely related to the key bisdihydropyridine intermediate 3 of the biogenetically unique manzamine family, has been efficiently achieved via stepwise inter- and intramolecular N-alkylations of 3-alkylpyridine derivatives 26 and 28. The first convergent total synthesis of biogenetically stimulating haliclamine A ( 1) has been efficiently accomplished via inter- and intramolecular N-alkylations of 3-alkylpyridine derivatives.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10368-9