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Titolo:
Efficient assembly of the phomactin core via two different macrocyclization protocols
Autore:
Houghton, TJ; Choi, S; Rawal, VH;
Indirizzi:
Univ Chicago, Dept Chem, Chicago, IL 60637 USA Univ Chicago Chicago IL USA 60637 icago, Dept Chem, Chicago, IL 60637 USA
Titolo Testata:
ORGANIC LETTERS
fascicolo: 23, volume: 3, anno: 2001,
pagine: 3615 - 3617
SICI:
1523-7060(20011115)3:23<3615:EAOTPC>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
ACTIVATING-FACTOR ANTAGONISTS; ACETYLENIC ALDEHYDES; PAF ANTAGONISTS; REAGENTS; ROUTE; ESPERAMICIN; KETONES; SUBUNIT; ANALOGS; ALKYNES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
38
Recensione:
Indirizzi per estratti:
Indirizzo: Houghton, TJ Univ Chicago, Dept Chem, 5735 S Ellis Ave, Chicago, IL 60637 USA Univ Chicago 5735 S Ellis Ave Chicago IL USA 60637 60637 USA
Citazione:
T.J. Houghton et al., "Efficient assembly of the phomactin core via two different macrocyclization protocols", ORG LETT, 3(23), 2001, pp. 3615-3617

Abstract

[GRAPHICS]The core structure of phomactins C and D was assembled by an efficient strategy starting from 3,4-dimethylcyclohexen-2-one. Key reactions include (1)a high yielding and highly diastereoselective Michael addition of a mixed cuprate, (2) a carbonylative alkyne-enoltriflate coupling or an intramolecular addition of an acetylide onto an aldehyde to form the macrocycle, (3) chemoselective Michael addition of a cuprate to an enynone, to give the carbon framework of desformyl phomactin C or D, and finally (4) regioselective addition of a thia-nucleophile to the more reactive beta -position of the resulting dienone.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/01/20 alle ore 10:13:24