Efficient and highly enantioselective formation of the all-carbon quaternary stereocentre of lyngbyatoxin A.
Indole 25, an advanced intermediate in a projected enantioselective total synthesis of lyngbyatoxin A 1, was prepared from allylic alcohol 11 in 9 steps and >95% ee, key transformations being the enantiospecific rearrangement of vinyl epoxide 14 and the Hemetsberger-Knittel reaction of azide 24.
Vital
Paulo
P
Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800, Kgs. Lyngby, Denmark.
Tanner
David
D
D000458:Cyanobacteria / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D008235:Lyngbya Toxins / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D007211:Indoles; D008235:Lyngbya Toxins