Convergent stereospecific total synthesis of monocillin I and radicicol: some simplifications and improvements

✍ Scribed by Isabelle Tichkowsky; Robert Lett

• Book ID: 104251131
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 304 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00713-x

✦ Synopsis

A much improved and reliable access to the macrolide 9, key-intermediate in our synthesis of monocillin I and radicicol is reported, via a modification of our first synthesis. The formation of the conjugated E,Z-dienone trans-epoxide is now achieved in a much higher yield, in a stereospecific reaction, by elimination of the methanesulfonate ester of the 6%-OH of the intermediate macrolide. It is also shown that the configuration of the 6%-OH has no significant incidence on all the steps leading to 9, and that consequently the two diastereoisomers 12, epimeric at 6%, can be used for the synthesis of radicicol.