Dolastatins. 26. Synthesis and Stereochemistry of Dolastatin 111a

RB Bates, KG Brusoe, JJ Burns, S Caldera…

Index: Bates, Robert B.; Brusoe, Kennard G.; Burns, Jennifer J.; Caldera, Sriyani; Cui, Wei; Gangwar, Sanjeev; Gramme, Michelle R.; McClure, Kelly J.; Rouen, Gregory P.; Schadow, Heiko; Stessman, Chad C.; Taylor, Stuart R.; Vu, Vicky H.; Yarick, Gayle V.; Zhang, Jianxing; Pettit, George R.; Bontems, Roger Journal of the American Chemical Society, 1997 , vol. 119, # 9 p. 2111 - 2113

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Citation Number: 50

Abstract

Because its three methyl groups attached to heteroatoms could be added simultaneously, dipeptide 14 was synthesized as a unit as shown in Scheme 2. To provide convergence in the synthesis, the Gly-N-Me-Leu-Gly tripeptide 19 was synthesized as shown in Scheme 3. Scheme 4 shows the assembly of the units used to synthesize dolastatin 11 (1). The hydroxyacid Hmp (22) was prepared from l-Ile by treatment with nitrous acid under conditions used on l-Leu ...

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