A concise route to the azaspirodecane moiety of halichlorine and structurally related alkaloids.
[reaction: see text] A tandem Michael addition-enolate alkylation followed by Dieckmann cyclization and Beckmann rearrangement provided the corresponding [5.4.0] azaspirobicyclodecane, a key intermediate in our synthetic route to the marine alkaloid halichlorine (1).
de Sousa
Andrea L
AL
Instituto de Química, Universidade Estadual de Campinas, C. P. 6154,13084-971, Campinas, SP, Brazil.
Pilli
Ronaldo A
RA
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D013141:Spiro Compounds; C412666:halichlorine