SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .1. SYNTHESIS OF ENANTIOMERIC PAIRS OF THE ABE RING-SYSTEMS OF QUINOCARCIN

Authors
SAITO S TAMURA O KOBAYASHI Y MATSUDA F KATOH T TERASHIMA S
Citation
S. Saito et al., SYNTHETIC STUDIES ON QUINOCARCIN AND ITS RELATED-COMPOUNDS .1. SYNTHESIS OF ENANTIOMERIC PAIRS OF THE ABE RING-SYSTEMS OF QUINOCARCIN, Tetrahedron, 50(21), 1994, pp. 6193-6208
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
21
Year of publication
1994
Pages
6193 - 6208
Database
ISI
SICI code
0040-4020(1994)50:21<6193:SSOQAI>2.0.ZU;2-F
Abstract
Enantiomeric pairs of the ABE ring system (5 and ent-5) and its analog ues (6, ent-6, 7, and ent-7) of quinocarcin (1), a prominent antitumor antibiotic, were synthesized in >95% ee with an aim to elucidate stru cture-activity relationships of 1. The key step of the synthesis inclu des novel diastereoselective reduction of 3,4-dihydroisoquinoline deri vatives 25 and ent-25, wherein each enantiomer of 4-O-benzyl-2,3-O-iso propylidene-threose (I and ent-I) is employed as a chiral auxiliary.