Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues.
[reaction: see text] Enantioselective synthesis of FR-900482 analogues is described. The key reaction of the synthesis is intramolecular 1,3-dipolar cycloaddition of a highly functionalized nitrile oxide with complete stereo- and regioselectivities to construct the eight-membered benzazocine ring.
Kambe
M
M
Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, The Japan Science and Technology Corporation, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Arai
E
E
Suzuki
M
M
Tokuyama
H
H
Fukuyama
T
T
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D003432:Cross-Linking Reagents; D018360:Crystallography, X-Ray; D003500:Cyclization; D010078:Oxazines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000903:Antibiotics, Antineoplastic; D003432:Cross-Linking Reagents; D010078:Oxazines; C053335:FR 900482