Concepedia

Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 3:  Synthesis of Fragment C<sub>15</sub><sub>-</sub><sub>21</sub>

Stuart J. Mickel, Gottfried Sedelmeier, Daniel Niederer, Friedrich Schuerch, Guido Koch, Ernst Kuesters, Robert Daeffler, Adnan Osmani, Manuela Seeger‐Weibel, Emil Schmid,

Organic Process Research & Development · 2003 · 66 citations · 8 references

DOI

Concepts

Abstract

Smith's procedure of preparing fragment C 15 - 21 ( 5 ) from common precursor 3 was optimized. The ease of plant operations made this six-step route successful for the production of several kilograms of this fragment with high purity.

References

8

Evolution of a Gram-Scale Synthesis of (+)-Discodermolide

Amos B. Smith, Thomas J. Beauchamp, Matthew J. LaMarche et al. · Journal of the American Chemical Society · 2000 · 236 citations

, , +15

Protection of hydroxy groups by intramolecular oxidative formation of methoxybenzylidene acetals with DDQ

Yuji Oikaw, Tadao Yoshioka, Osamu Yonemitsu · Tetrahedron Letters · 1982 · 177 citations

, , +7

A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp<sub>2</sub>Zr(H)Cl

Jonathan M. White, Ashok Rao Tunoori, Gunda I. Georg · Journal of the American Chemical Society · 2000 · 154 citations

, , +6

Improved Procedure for the Reduction of N-Acyloxazolidinones

Thomas D. Penning, Stevan W. Djurić, Richard A. Haack et al. · Synthetic Communications · 1990 · 143 citations

, , +1

Gram-Scale Synthesis of (+)-Discodermolide

Amos B. Smith, Michael D. Kaufman, Thomas J. Beauchamp et al. · Organic Letters · 1999 · 121 citations

, , +4