Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: Solvent effect on the stereochemistry of …

P Magnus, JS Mendoza, A Stamford…

Index: Magnus, Philip; Mendoza, Jose S.; Stamford, Andrew; Ladlow, Mark; Willis, Paul Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10232 - 10245

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Citation Number: 80

Abstract

Abstract: The overall strategy for the synthesis of vinblastine (1) is based upon the nonoxidative cleavage of the tertiary amine (+)-18 to generate the intermediate delocalized cation Ma, which in the presence of an electron-rich aromatic nucleophile can be trapped at C-18'to give the bisalkaloid analogues 19, 20, and 21. To ascertain the effect on (2- 18'stereochemistry with respect to C-2'and C-4'stereochemistry, we have made a number ...