Diamine alkaloids, polycyclic

Polycyclic Diamine Alkaloids from Marine Sponges... 

Marine sponges are a source of an array of polycyclic diamine alkaloids of common biogenetic origin. This class of secondary metabolites has been the subject of four previous reviews [4-7]. Therefore, the present review will include literature reports previously not discussed, dealing with the isolation, structure determination, biological activities, and total synthesis of polycycUc diamine alkaloids isolated from marine sponges. This review will not include guanidine alkaloids [8,9] or the manzamine alkaloids [10,11], since these compounds have been recently reviewed elsewhere. Only polycycUc... 

Berlinck RGS (2007) Polycyclic Diamine Alkaloids from Marine Sponges. 10 211-238 Besson T, Thiery V (2006) Microwave-Assisted Synthesis of Sulfur and Nitrogen-Containing Heterocycles. 1 59-78... 

ABSTRACT Marine sponges have frequently afforded a wide variety of alkaloids. Polycyclic amines (3-alkylpiperidine alkaloids) are secondary metabolites that are profusely found in Indo-Pacific sponges. These compounds contain complicated skeletons with several macrocyclic rings. One of the first members of these exclusively sponge-derived alkaloids is manzamine A, which was described independently by Riga in 1986 and by Nakamura in 1987. This compound possesses an unusual pentacyclic diamine fused ring joined to Cl of a )S-carboline moiety. 

Scheme 40. A biomimetic approach to the polycyclic diamine alkaloids model studies.

Primary and secondary amines also react with epoxides (or in situ produced episulfides )r aziridines)to /J-hydroxyamines (or /J-mercaptoamines or 1,2-diamines). The Michael type iddition of amines to activated C—C double bonds is also a useful synthetic reaction. Rnally unines react readily with. carbonyl compounds to form imines and enamines and with carbo-tylic acid chlorides or esters to give amides which can be reduced to amines with LiAlH (p. Ilf.). All these reactions are often applied in synthesis to produce polycyclic alkaloids with itrogen bridgeheads (J.W. Huffman, 1967) G. Stork, 1963 S.S. Klioze, 1975). 

Although several synthetic approaches have been developed toward the total synthesis of polycyclic diamine sponge alkaloids, only a few members of this class have been synthesized. 

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