Marine macrolide glycosides

Lyngbyaloside B, a Marine Macrolide Glycoside Total Synthesis and Stereochemical Revision... 

Pathirana, C., Tapiolas, D.M., Jensen, P.R., Dwight, R., and Fenical, W., Structure determination of maduralide a new 24-membered ring macrolide glycoside produced by a marine bacterium (Actino-... 

Marine macrolides have numerous asymmetric centers, oxygenated function-ahties including alcohols, carbonyl groups, the tetrahydropyran moiety, di-and trisubstituted alkenes, and macrocycUc lactones. For completion of their total synthesis, efficient and stereoselective introduction of these characteristic units should be crucial. Recently, an excellent review on asymmetric synthesis of 1,3-diol, macrolactonization, and glycosidation in the syntheses of macrolides has been pubUshed by Nakata [5]. The multisubstituted tetrahydropyran moieties are often found in the marine macrohdes, and the efficient preparation of these moieties is recognized as the key reaction in their total synthesis. In this decade, efficient methods for their stereoselective construction have been developed and used in the total synthesis of marine macrolides, wherein the relative configuration of 2- and 6-substituents is pivotal. In this section, recent progress in the preparation of tetrahydropyrans is described (for a previous review on the preparation of tetrahydropyrans, see [9]). 

FIG. 2 Structures of macrolide glycosides from marine cyanobacteria. 

Teruya, T, Sasaki, H Kitamura, K Nakayama, T, and Suenaga, K. (2009a) Biselyngbyaside, a macrolide glycoside from the marine cyanobacterium Lyngbya sp. Org. Lett., 11, 2421-2424. 

MacMillan, J.B., Xiong-Zhou, G Skepper, C.K., and Molinski, T.F. (2008) Phorbasides A-E, cytotoxic chlorocyclopropane macrolide glycosides from the marine sponge Phorbas sp. CD determination of C-methyl sugar configurations. J. Org. Chem., 73, 3699-3706. 

Sone, H., Suenaga, K., Bessho, Y, Kondo, X, Kigoshi, H., and Yamada, K. (1998) Synthesis of the aglycon of aurisides A and B, cytotoxic macrolide glycosides of marine origin. Chem. Lett, 85-86. 

Erickson, K.L., Gustafson, K.R., Pannell, L.K., Beutler, JA., and Boyd, M.R. (2002) New dimeric macrolide glycosides from the marine sponge Myriastra davosa, J, Nat, Prod., 65,1303-1306. 

Zampella A, D Auria MV, Minale L, Debitus C (1997) Callipeltosides B and C, Two Novel Cytotoxic Glycoside Macrolides from a Marine Lithistida Sponge Callipelta sp. Tetrahedron 53 3243... 

LueschH, YoshidaWY, HarriganGG, Doom JP, Moore RE, Paul VJ (2002) Lyngbyaloside B, a New Glycoside Macrolide from a Palauan Marine Cyanobacterium, Lyngbya sp. J Nat Prod 65 1945... 

Tan, L.T, Marquez, B.L., and Gerwick, W.H. 2002. Lyngbouilloside, a Novel Glycosidic Macrolide from file Marine Cyanobacterium Lyngbya Bouillonii. Journal of Natural Products 65(6), 925-928. 

A Palauan collection of the marine cyanobacterium Lyngbya sp. yielded a new glycoside macrolide, lyngbyaloside B 102. Lyngbyaloside B was weakly cytotoxic against KB cells with an IC50 value of 4.3jaM and exhibited a considerably smaller effect on LoVo cells (ICso lS pM). The... 

Zampella, A., D Auria, M.V., Minale, L., and Debitus, C. (1997) Callipeltosides B and C, two novel cytotoxic glycosides macrolides from a marine Lithistida sponge Callipelta sp. Tetrahedron, 53, 3243-3248. 

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