ChemInform Abstract: Application of a Stereospecific Intramolecular Allenylsilane Imino Ene Reaction to Enantioselective Total Synthesis of the 5,11- Methanomorphanthridine Class of Amaryllidaceae Alkaloids.

✍ Scribed by J. JIN; S. M. WEINREB

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199741268

✦ Synopsis

Application of a Stereospecific Intramolecular Allenylsilane Imino

Ene Reaction to Enantioselective Total Synthesis of the 5,11-Methanomorphanthridine Class of Amaryllidaceae Alkaloids.

-Starting from the enantiomerically pure epoxy alcohol (I) the allenylsilane aldehyde (II) is prepared. Its use in an intramolecular concerted pericyclic allenylsilane imino ene cycloaddition as a key step yields the target intermediate cis-amino alkyne (IV). It can be transformed into the enantiomerically pure title alkaloids, montanine ( Va), coccinine (Vb) and pancracine (Vc). -(JIN, J.;