Antineoplastic agents. 571. Total synthesis of bacillistatin 2.
The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.
Pettit
George R
GR
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, USA. bpettit@asu.edu
Hu
Shougang
S
Knight
John C
JC
Chapuis
Jean-Charles
JC
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D066298:In Vitro Techniques; D007941:Leukemia P388; D008297:Male; D051379:Mice; D015394:Molecular Structure; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D047630:Depsipeptides; D044950:Flavanones; D006027:Glycosides; C548570:bacillistatin 2; C548695:mattucinol-7-O-(4'',6''-O-(aS)-hexahydroxydiphenoyl)-beta-D-glucopyranoside