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Synthesis of marine guanidine alkaloids and their application as chemical/biological tools
Author(s) -
Nagasawa Kazuo,
Hashimoto Yuichi
Publication year - 2003
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.10064
Subject(s) - guanidine , cycloaddition , chemistry , combinatorial chemistry , biomimetic synthesis , organic chemistry , catalysis
Ptilomycalin A and crambescidins, novel marine guanidine alkaloids, have a unique pentacyclic guanidine structure, and exhibit a considerable array of biological activities. The first method developed for the synthesis of the pentacyclic guanidine core structure involved successive 1,3‐dipolar cycloaddition reactions and resulted in the first total synthesis of crambescidin 359. The synthesis of other pentacyclic guanidine derivatives has been based on this methodology and applied as tools for studying biological activities, and as chemical reaction catalysts. © 2003 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 3: 201–211; 2003: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.10064