Synthesis of Two New Maytansinoid Model Compounds from Carbohydrate Precursors

Autor:	Omer L. Shedd, Heidi M. Crane, Joseph W. Thompson, Christine D. LaRocca, Brock K. King, Charles C. Harmon, Robert L. Lile, Thomas E. Goodwin, Shari G. Orlicek, John S. Swanson, Ronald W. Pelton, Phyllis O. Eason, Kimberley R. Cousins, Timothy E. Freyaldenhoven
Rok vydání:	1998
Předmět:	chemistry.chemical_classification Allylic rearrangement Natural product Sulfide Stereochemistry Organic Chemistry Sulfoxide Alkylation Maytansinoid Ring (chemistry) Biochemistry chemistry.chemical_compound chemistry Derivative (chemistry)
Zdroj:	Journal of Carbohydrate Chemistry. 17:323-339
ISSN:	1532-2327 0732-8303
DOI:	10.1080/07328309808002895
Popis:	Maytansine (1) is a macrocyclic natural product with significant anti-cancer activity. A derivative (4) of D-glucal is converted to a model compound (10) for the lower periphery of the maytansinoid ring via alkylation at C-6 using an allylic sulfide anion, followed by oxidation to the sulfoxide and [2,3]-sigmatropic rearrangement to the sulfenate ester. In addition, a method is disclosed for conversion of D-arabinose to a chiron (18) for a portion of the upper periphery of the maytansinoids.
Databáze:	OpenAIRE
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