Abstract
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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Depsipeptides / chemical synthesis*
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Depsipeptides / chemistry
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Depsipeptides / pharmacology*
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Drug Screening Assays, Antitumor
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Female
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Flavanones / chemistry*
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Flavanones / isolation & purification
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Glycosides / chemistry*
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Glycosides / isolation & purification
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Humans
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In Vitro Techniques
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Leukemia P388
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Male
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Mice
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Molecular Structure
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Stereoisomerism
Substances
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Antineoplastic Agents
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Depsipeptides
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Flavanones
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Glycosides
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bacillistatin 2
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mattucinol-7-O-(4'',6''-O-(aS)-hexahydroxydiphenoyl)-beta-D-glucopyranoside