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Titolo:
STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN AND RELATED-COMPOUNDS .2. DIELS-ALDER ADDITION OF N-ACYL DEHYDROALANINE ESTERS TO 1-TRIMETHYLSILYLOXYCYCLOHEXA-1,3-DIENE
Autore:
CROSSLEY MJ; STAMFORD AW;
Indirizzi:
UNIV SYDNEY,SCH CHEM SYDNEY NSW 2006 AUSTRALIA
Titolo Testata:
Australian Journal of Chemistry
fascicolo: 9, volume: 47, anno: 1994,
pagine: 1695 - 1711
SICI:
0004-9425(1994)47:9<1695:SDTTTS>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
BACILYSIN; PRODUCTS; REVISION; ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
29
Recensione:
Indirizzi per estratti:
Citazione:
M.J. Crossley e A.W. Stamford, "STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN AND RELATED-COMPOUNDS .2. DIELS-ALDER ADDITION OF N-ACYL DEHYDROALANINE ESTERS TO 1-TRIMETHYLSILYLOXYCYCLOHEXA-1,3-DIENE", Australian Journal of Chemistry, 47(9), 1994, pp. 1695-1711

Abstract

In a study directed towards the total synthesis of anticapsin and related compounds, the Diels-Alder addition of N-acyl dehydroalanine esters (15)-(19) to 1-trimethylsilyloxycyclohexa-1,3-diene (6) was investigated. The cycloadditions were highly regioselective and provided ethylsilyloxybicyclo[2.2.2]oct-5-ene-2-carboxylate derivatives (23)-(28) in moderate to good yields. A modest stereoselectivity was observed in the reactions, with the endo-adducts (23a)-(28a) favoured over the exo-adducts (23b)-(28b) by a ratio of 1.5-3.3:1. Adducts (23a) and (24a) underwent stereoselective epoxidation to the less hindered face of theolefinic double bond. Reaction of the resultant epoxides (31) and (32) with TiCl4 afforded carbolactones (34) and (35), thereby allowing the assignment of endo stereochemistry to adducts (23a) and (24a). The stereochemistry of the remaining adducts was assigned by the use of H-1n.m.r. spectroscopy.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 24/09/20 alle ore 21:28:22