Total synthesis of (+/-)-chartelline C.
The first total synthesis of (+/-)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive beta-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.
Baran
Phil S
PS
Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.
Shenvi
Ryan A
RA
D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; C513615:chartelline