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Titolo:
STEREOCONTROLLED SYNTHESIS OF MULTIFUNCTI ONAL BIOACTIVE COMPOUNDS
Autore:
ISOBE M;
Indirizzi:
NAGOYA UNIV,FAC AGR,CHIKUSA KU NAGOYA AICHI 46401 JAPAN
Titolo Testata:
Yuki Gosei Kagaku Kyokaishi
fascicolo: 1, volume: 55, anno: 1997,
pagine: 44 - 55
SICI:
0037-9980(1997)55:1<44:SSOMOB>2.0.ZU;2-T
Fonte:
ISI
Lingua:
JPN
Soggetto:
FUSED POLYETHER TOXINS; ANTI-TUMOR LACTONES; HETEROCONJUGATE ADDITION; OKADAIC ACID; ACYCLIC STEREOCONTROL; ASYMMETRIC INDUCTION; NICHOLAS REACTION; GENERAL-APPROACH; HETERO-OLEFINS; ALKYNYL SUGARS;
Keywords:
STEREOCONTROLLED SYNTHESIS; SUBSTRATE CONTROL (DIASTEREO-SELECTION); REAGENT CONTROL (ENANTIO-SELECTION); VERNOLEPIN; MAYTANSINE; OKADAIC ACID; TAUTOMYCIN PROSTAGLANDIN; PRELOG-DJERASSI LACTONE; LAMPTEROFLAVIN; ENDIYNE; HETEROCONJUGATE ADDITION; NICHOLAS REACTION; SUGAR ACETYLENE; ACETYLENE BISCOBALTHEXACARBONYL COMPLEX; A-STRAIN (ALLYLIC STRAIN); C-GLYCOSIDATION; ALPHA CHELATION AND BETA CHELATION; SWITCHING DIASTEREOSELECTIVITY; SWITCHING ENANTIOSELECTIVITY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
57
Recensione:
Indirizzi per estratti:
Citazione:
M. Isobe, "STEREOCONTROLLED SYNTHESIS OF MULTIFUNCTI ONAL BIOACTIVE COMPOUNDS", Yuki Gosei Kagaku Kyokaishi, 55(1), 1997, pp. 44-55

Abstract

Synthetic strategy and concept of multi-step synthesis of biologically important compounds are discussed with special reference under stereochemical control. A-strain in cyclic exo-olefin was expanded to acyclic cases to allow high stereoselectivity in conjugate addition, epoxidation, etc. A special synthetic methodology named heteroconjugate addition has been improved in various aspects (i) preparation of heteroolefin, (ii) diastereo-switching of syn or anti product, (iii) enantio-switching of D or L from D-sugar analog and (IV) coupling with other fragments in the total syntheses of maytansinoids, okadaic acid, tautomycin, etc. Recent advances on sugar acetylene chemistry are also introduced to use the corresponding biscobalthexacarbonyl complexes and Nicholas type reaction for medium-size ether ring formation. These syntheses request multiple organic reactions such as carbanions, carbenium cations, organometallic reagents, heteroatom chemistry for bond formationin good harmony with functional group preparation of the target natural products.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 10/07/20 alle ore 03:16:13