Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1:  Synthetic Strategy and Preparation of a Common Precursor

Autor: Mickel, S. J., Sedelmeier, G. H., Niederer, D., Daeffler, R., Osmani, A., Schreiner, K., Seeger-Weibel, M., Berod, B., Schaer, K., Gamboni, R., Chen, S., Chen, W., Jagoe, C. T., Kinder, F. R., Jr., Loo, M., Prasad, K., Repic, O., Shieh, W.-C., Wang, R.-M., Waykole, L., Xu, D. D., Xue, S.
Zdroj: Organic Process Research & Development; January 2004, Vol. 8 Issue: 1 p92-100, 9p
Abstrakt: The synthetic strategy for producing multigram quantities of (+)-discodermolide (1) using a hybridized Novartis−Smith−Paterson synthetic route via common precursor 3 is described. In the first part of this five-part series, we present a multikilogram preparation of α-methyl aldehyde 10 from Roche ester, its syn-aldol reaction with Evans boron enolate, removal of the chiral auxiliary, and the preparation of Weinreb amide 3 (Smith common precursor). The common precursor was produced without any chromatography.
Databáze: Supplemental Index