Aurisides

The macrolide glycosides, aurisides A (17) and B (18), from the Japanese sea hare Dolabella auricularia show cytotoxicity against HeLa S3 cells with IC50 values of 0.17 and 1.2 pg/ml, respectively [35]. 

Sone H, Kigoshi H, Yamada K (1996) Aurisides A and B. Cytotoxic Macrolide Glycosides from the Japanese Sea Hare Dolabella auricularia. J Org Chem 61 8956... 

Paterson I, Florence GJ, Heimann AC, Mackay AC (2005) Stereocontrolled Total Synthesis of (-)-Aurisides A and B. Angew Chem Int Ed 44 1130... 

Critical data (a) the revised structure was proposed by comparison of the H NMR data to those of callipeltoside A and aurisides A and B with same macrocyclic ring system, (b) the spectral data of the revised structure by the total synthesis were identical to those of the natural product, (c) [ ] +2.2 (synthetic product), [ ]d +7.5 (natural product). 

Sone, H., Kigoshi, H., and Yamada, K. (1996). Aurisides A and B, cytotoxic macrolide glycosides from the Japanese sea hare Dolabella auricularia. J. Org. Chem. 61, 8956-8960. 

Sensitive Deprotections. Since the previous review, TASF has emerged as a good alternative to TBAF for the mild deprotection of silyl ethers of acid- and/or base-sensitive corr5>ounds. Side reactions, commonly observed during deprotection using TBAF, include complete decomposition (encountered during the synthesis of amphidinolides and aurisides ), acyl migra-... 

Aurisides A and B, Kigoshi Azapriacid-1, Nicolaou 57 vinvl indirlf 90% vinyl iodide, 95%... 

A similar reaction was used for preparation of the remote stereocenter in 85, an intermediate in Paterson s synthesis of aurisides A and B. The asymmetric catalysis of the aldol reaction with fluoral has also been investigated by Mikami for highly enantioselective syntheses of fluorine-containing aldols. The reaction of the ketene trimethylsilyl acetal 86 with fluoral (87) in the presence of the BfNOL-catalyst 67 yielded the aldol adduct 88 in moderate yield (56%) and high enantioselectivity (90% ee). 

Suenaga, K., Hoshino, H., Yoshii, X, Mori, K Sone, H Bessho, Y Sakakura, A Hayakawa, I., Yamada, K., and Kigoshi, H. (2006) Enatioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin. Tetrahedron, 62, 7687-7698. 

Xello-Aburto, R., Ochoa-Xeran, A., and Olivo, H.F. (2006) Model studies on the ring construction of the auriside macrolactone. Tetrahedron Lett., 47, 5915-5917. 

Bourcet, E., Eache, F., and Piva, O. (2009) Access to the core structure of aurisides by a ring-closing. Tetrahedron Lett., 50,1787-1790. 

Aiorisides A and B are a-i-rhamnosides (6-deoxymanno-sides) of brominated macrolides that have been isolated from the species Dolabdla auricularia at particularly low levels 0.8 and 0.7 mg, respectively, from 278 kg of mollusk (Sone, Kiguchi, and Yamada, 1996a). These glycosides are cytotoxic to adenocarcinoma HeLa-S3 cells with ID50 values of 0.17 and 1.2 pg ml , respectively. The 6-deoxyman-nose of auriside B has a very unusual carbamic ester. 

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