Synthesis of Two New Maytansinoid Model Compounds from Carbohydrate Precursors

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...

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Bibliographic Details
Published in:	Journal of carbohydrate chemistry Vol. 17; no. 3; pp. 323 - 339
Main Authors:	Goodwin, Thomas E., Cousins, Kimberley R., Crane, Heidi M., Eason, Phyllis O., Freyaldenhoven, Timothy E., Harmon, Charles C., King, Brock K., LaRocca, Christine D., Lile, Robert L., Orlicek, Shari G., Pelton, Ronald W., Shedd, Omer L., Swanson, John S., Thompson, Joseph W.
Format:	Journal Article
Language:	English
Published:	Taylor & Francis Group 01-04-1998
Online Access:	Get full text
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Summary:	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.
ISSN:	0732-8303 1532-2327
DOI:	10.1080/07328309808002895