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Titolo:
ASYMMETRIC OXIDATIVE CYCLIZATION OF O-PHENOLIC OXIME-ESTERS - FIRST SYNTHESIS OF ENANTIOMERICALLY ENRICHED SPIROISOXAZOLINE METHYL-ESTERS
Autore:
MURAKATA M; TAMURA M; HOSHINO O;
Indirizzi:
SCI UNIV TOKYO,FAC PHARMACEUT SCI,SHINJUKU KU,12 ICHIGAYA FUNAGAWARA MACHI TOKYO 162 JAPAN SCI UNIV TOKYO,FAC PHARMACEUT SCI,SHINJUKU KU TOKYO 162 JAPAN
Titolo Testata:
Journal of organic chemistry
fascicolo: 13, volume: 62, anno: 1997,
pagine: 4428 - 4433
SICI:
0022-3263(1997)62:13<4428:AOCOOO>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
SPONGE; DERIVATIVES; (+/-)-HOMOAEROTHIONIN; (+/-)-AEROTHIONIN; FISTULARIN-3; METABOLITES; INDUCTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
28
Recensione:
Indirizzi per estratti:
Citazione:
M. Murakata et al., "ASYMMETRIC OXIDATIVE CYCLIZATION OF O-PHENOLIC OXIME-ESTERS - FIRST SYNTHESIS OF ENANTIOMERICALLY ENRICHED SPIROISOXAZOLINE METHYL-ESTERS", Journal of organic chemistry, 62(13), 1997, pp. 4428-4433

Abstract

A new method for the synthesis of enantiomerically enriched cyclohexadienone spiroisoxazoline (-)-2a has been described. Asymmetric intramolecular oxidative cyclization of the o-phenolic oxime-ester Ic using anovel optically active tertiary alcohol (-)-3 as a chiral auxiliary proceeded smoothly to afford cyclohexadienone spiroisoxazoline 2c in 83% yield. Opitcally active tertiary alcohol (-)-3 was synthesizied, from racemic (1S, 8R*, 9R*, 10R*)-8-phenyl-1-decalol (4) by optical resolution. Removal of the chiral auxiliary in 2c with CF3COOH followed bymethylation gave methyl ester (-)-2a in 74% ee (71% chemical yield) having S-configuration. The absolute configuration of 2a was determinedby the synthesis of the marine natural product (+)-aerothionin.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 14/08/20 alle ore 07:22:13