Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2:  Synthesis of Fragments C1-6 and C9-14

Stuart J. Mickel,* Gottfried H. Sedelmeier, Daniel Niederer, Friedrich Schuerch, Dominique Grimler, Guido Koch, Robert Daeffler, Adnan Osmani, Alfred Hirni, Karl Schaer, and Remo Gamboni
Chemical and Analytical Development, Novartis Pharma AG, CH 4002 Basel, Switzerland
Andrew Bach, Apurva Chaudhary, Stephen Chen, Weichun Chen, Bin Hu, Christopher T. Jagoe, Hong-Yong Kim, Frederick R. Kinder, Jr., Yugang Liu, Yansong Lu, Joseph McKenna, Mahavir Prashad, Timothy M. Ramsey, Oljan Repi, Larry Rogers, Wen-Chung Shieh, Run-Ming Wang, and Liladhar Waykole
Novartis Institutes for Biomedical Research, One Health Plaza, East Hanover, New Jersey 07936, U.S.A.
Org. Proc. Res. Dev., 2004, 8 (1), pp 101–106
DOI: 10.1021/op0341317
Publication Date (Web): December 4, 2003
Copyright © 2004 American Chemical Society
*

 Corresponding author:  E-mail:  stuart_john.mickel@pharma.novartis.com.

Abstract

Abstract Image

Kilogram-scale syntheses of fragments C1-6 (6) and C9-14 (4) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation of byproducts that were isolated and characterized in Smith's synthesis.

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History

  • Published In Issue January 16, 2004
  • Received for review September 16, 2003.

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