Remote stereochemical control in asymmetric Diels–Alder reactions: synthesis of the angucycline antibiotics, (−)-tetrangomycin and MM 47755

✍ Scribed by John S. Landells; David S. Larsen; Jim Simpson

• Book ID: 104253901
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 173 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01228-0

✦ Synopsis

The first asymmetric syntheses of the angucycline antibiotics, (-)-tetrangomycin and MM 47755, are achieved via a short efficient sequence starting from the chiral Lewis acid promoted Diels-Alder reaction of 5-hydroxy-1,4-naphthoquinone and (±)-(E)-5-dimethylphenylsilyl-5-methyl-1-(2%-trimethylsiloxyvinyl)cyclohexene 7 where an effective kinetic resolution of the latter, controlled by its remote stereocentre, is described.