Health & Environmental Research Online (HERO)


Print Feedback Export to File
8149368 
Journal Article 
Remote stereochemical control in asymmetric Diels-Alder reactions: Synthesis of the angucycline antibiotics, (-)-tetrangomycin and MM 47755 
Landells, JS; Larsen, DS; Simpson, J 
2003 
1 
Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581 
Elsevier Ltd 
44 
28 
5193-5196 
English 
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. © 2003 Elsevier Science Ltd. All rights reserved.