The esperamicins

Esperamicin A, (3) Esperamicin An, Esperamicin A Esperamicin P Esperamicin Aj Esperamicin A2), Esperamicin Aj  

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Bicyclic Core of the Esperamicin/Calichemicin Class of Antitumor Agents... 

Prabhakaran, J. Lhermitte, H. Das, J. Sasi-Kumar, T.K. Grierson, D.S. The synthesis of a sulfone containing analogue of the esperamicin-A(l) aglycone A hetero Diels-Alder approach. Synlett 2000, 658-662. 

Crevisy, C. Beau, J.-M. The esperamicin-calicheamicin aglycones ring closure of a simple strained system mediated by chromium(II)-nickel(ll) salts. Tetrahedron Lett. 1991, 32, 3171-3174. 

Magnus, P., Lewis, R.T., and Bennett, E, Synthesis of the esperamicin Aj/calicheamicin y-trisulphide functionaUty. Thermal stability and reduction, 7. Chem. Soc., Chem. Commun., 916, 1989. 

In a model reaction for the preparation of the esperamicin/calicheamicin aglycones (Scheme 2-20) the enediyne alcohol 175 is converted into the terminal iodo derivative 176 by... 

Scheme 7-45 An intramolecular Diels-Alder approach to the esperamicin enediyne core (Schreiber and co-workers).

Scheme 7-60 Synthesis of the esperamicin A, trisaccharide 288 (Danishefsky and co-workers). (PMB, p-methoxybenzyl TEOC, 2-(trimethylsilyl)ethoxycarbonyl).

Smbbe J, KozarichJW, Doyle TU. Umnasking the chemistry of DNA cleavage by the esperamicins Modulation of 4 -hydrogen abstraction and bistranded damage by the fucose-anthranilate moiety. Chem Soc. 1992 114 8763. 

Epstein JL, ZhangX, Doss GA, et al. Interplay of hydrogen abstraction and radical repair in the generation of single- and double-strand DNA damage by the esperamicins. J Am Chem Soc. 1997 119 6731-6738. 

Cycloaddition of nitrones to 5,6-dideoxy-l,2-0-isopropylidene-a-D-jcy/o-hex-5-enofuranose gave mainly or exclusively the cw-substituted isoxazolines 49. The hydroxylamine-linkage of the esperamicin trisaccharide 51 was constructed by 0-glycosylation of the nitrone 50 followed by deprotection (Scheme 11). ... 

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