Grubbs' RCM in the Total Synthesis of the Microtubule Stabilizing Drug Laulimalide

✍ Scribed by Johann Mulzer; Elisabeth Öhler; Valentin S. Enev; Martin Hanbauer

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 227 KB
• Volume: 344
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/1615-4169(200208)344:6/7<573::aid-adsc573>3.0.co;2-c

✦ Synopsis

Two independent syntheses of the microtubule stabilizing antitumor agent laulimalide are described, which mainly differ with respect to the macrocyclization step. The first synthesis employs a Still±Gennari olefination and the second one an Alexakis-type, allylsilane/acetal addition to close the final ring. For the construction of the dihydropyran subunits, RCM methodology and alternative strategies are presented in comparison. 1 Introduction 2 Still±Gennari Macrocyclization Route 3 Allylsilane/Acetal Macrocyclization Route 4 Conclusion