New stereoselective entry to azaspirocyclic nucleus of halichlorine and pinnaic acids by radical translocation/cyclization reaction.
[reaction: see text] A stereoselective approach to the spirocyclic nucleus of halichlorine and pinnaic acids has been developed starting from a piperidine derivative. A key transformation in this sequence involves a cascade radical translocation/cyclization process.
Takasu
Kiyosei
K
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan. mihara@mail.pharm.tohoku.ac.jp
Ohsato
Hiroshi
H
Ihara
Masataka
M
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001391:Azo Compounds; D005609:Free Radicals; D010880:Piperidines; D013141:Spiro Compounds; C412666:halichlorine; C412665:pinnaic acid