Cationic reduction of bastadin-4 to bastadin-5. Preparation of 5-[2h]-bastadin-5 by site-specific isotopic labeling.
A chemoselective conversion of bastadin-4 to the important Ca2+ channel modulator bastadin-5 (1a) has been achieved using cationic hydrogenation (Et3SiH, TFA, 60%). Specifically deuterated bastadin-5 (1b, >95 at. %) was prepared following this method and the simplified 1H NMR H-5/H2-6 spin system of 1b exploited to study temperature-dependent macrocyclic ring dynamics.
Masuno
Makoto N
MN
Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Molinski
Tadeusz F
TF
D000818:Animals; D002120:Calcium Channel Agonists / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D055768:Halogenated Diphenyl Ethers; D006865:Hydrogenation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010647:Phenyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D013696:Temperature
D002120:Calcium Channel Agonists; D055768:Halogenated Diphenyl Ethers; D010647:Phenyl Ethers; C474669:bastadin 4; C105188:bastadin 5