Synthesis of 3,4-Di-O-benzyl-1-O-methyl-L-galactitol, a key precursor of the C33-C37 fragment of calyculins

Journal of the Brazilian Chemical Society

Varela, Oscar¹  Cironi, Pablo¹  Universidad de Buenos Aires, Ciudad Universitaria, Argentina¹ 

关键词: calyculins;    secondary metabolites;    marine sponge;    galactose diacetonide;    L-galactitol derivative.;   

DOI  :  10.1590/S0103-50532001000500010

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The calyculins A-H are the secondary metabolites isolated from the Japonese marine sponge Discodermia calyx which exhibited varied biological activities, including antitumor, smooth muscle contractile and tumor promotion1,2. The basic structure of these polyketides differ mainly by a methyl group on C-32 and the geometry of C-2,3 and C-6,7 olefins. From the same sponge four new calyculins have been isolated more recently3, and also calyculins A, B, E and F and a mixture of calyculinamides A and B have been isolated from the New-Zeeland deep-water marine sponge Lamellomorpha strongylata4. Hydrolysis of calyculins affored 2,3-dihydroxy-4-dimethylamino-5-methoxypentanoic acid (2b), the C33-C37 fragment of the molecule, which has a (2S, 3S, 4S) configuration. The synthesis of its enantiomer from (S)-pyroglutaminol provided the conclusive evidence on the absolute configuration of calyculins5.Many efforts have been directed towards the synthesis of calyculins, and a carbohydrate approach to the synthesis of 2a has been reported6a. In this

【 授权许可】

Unknown