New achievements in the field of intramolecular phenolic coupling reactions, using hypervalent (III) iodine reagent: Synthesis of galanthamine

Authors
Krikorian, D Tarpanov, V Parushev, S Mechkarova, P
Citation
D. Krikorian et al., New achievements in the field of intramolecular phenolic coupling reactions, using hypervalent (III) iodine reagent: Synthesis of galanthamine, SYN COMMUN, 30(16), 2000, pp. 2833-2846
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
16
Year of publication
2000
Pages
2833 - 2846
Database
ISI
SICI code
0039-7911(2000)30:16<2833:NAITFO>2.0.ZU;2-V
Abstract
Our investigations on the oxidative possibilities of the hypervalent iodine (III) reagent established that phenyliodine(III)bis(trifluoroacetate) (PIFA ) can provide one-pot contiguous coupling-cyclization reaction giving a pro duct with narwedine skeleton, when used in a phenolic coupling reaction of p'-bromonorbelladine derivatives. A suitably selected precursor gave up to 60% yield of the coupled product.