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Titolo:
TOTAL SYNTHESIS OF TAUTOMYCIN
Autore:
OIKAWA M; UENO T; OIKAWA H; ICHIHARA A;
Indirizzi:
OSAKA UNIV,FAC SCI,DEPT CHEM TOYONAKA OSAKA 560 JAPAN HOKKAIDO UNIV,FAC AGR,DEPT BIOSCI & CHEM,KITA KU SAPPORO HOKKAIDO 060JAPAN
Titolo Testata:
Yuki Gosei Kagaku Kyokaishi
fascicolo: 12, volume: 53, anno: 1995,
pagine: 1123 - 1132
SICI:
0037-9980(1995)53:12<1123:TSOT>2.0.ZU;2-Z
Fonte:
ISI
Lingua:
JPN
Soggetto:
PROTEIN PHOSPHATASE INHIBITOR; FORMAL TOTAL SYNTHESIS; MACROLIDE TOTAL SYNTHESIS; CROSS-ALDOL REACTIONS; ACYCLIC STEREOSELECTION; ERYTHRONOLIDE-A; STEREOCONTROLLED SYNTHESIS; ABSOLUTE-CONFIGURATION; ADDITION-REACTIONS; CARBONYL-COMPOUNDS;
Keywords:
TAUTOMYCIN; PROTEIN PHOSPHATASE INHIBITOR; TOTAL SYNTHESIS; SPIROKETAL REDUCTION; REMOTE STEREOCHEMICAL CONTROL; ALDOL REACTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
69
Recensione:
Indirizzi per estratti:
Citazione:
M. Oikawa et al., "TOTAL SYNTHESIS OF TAUTOMYCIN", Yuki Gosei Kagaku Kyokaishi, 53(12), 1995, pp. 1123-1132

Abstract

The first synthesis of the antifungal antibiotic tautomycin, a potentprotein phosphatase inhibitor, has been achieved via aldol coupling of two large subunits, a right-hand C-1-C-21 ketone and a left-hand aldehyde (left from C-22). The C-1-C-10 segment;was synthesized through aremote stereochemical control process using a spiroketal template. After joining with the C-11-C-18 segment, the spiroketal moiety was selectively constructed. Then the right-hand C-1-C-21 ketone was synthesized via Roush asymmetric crotylboration. The left-hand aldehyde was prepared by esterification of a C-21-C-26 segment and a dialkylmaleic anhydride segment. The C-21-C-26 segment was synthesized through a regioselective opening of an epoxy alcohol, and the dialkylmaleic anhydride segment was through a diastereoselective olefination. Completely stereoselective assemblage of the two sub-units, the right-hand and the left-hand, was achieved employing the Mukaiyama aldol reaction. Further functional group manipulations including desilylation, oxidation at C-2, and deprotection of tert-butyl ester with concomitant anhydride formation provided tautomycin which was identical with the natural product. As a preliminary study, derivatizations and degradation of the natural product were also examined to support the total synthesis.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 15/07/20 alle ore 04:53:33