Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues

M Kambe; E Arai; M Suzuki; H Tokuyama; T Fukuyama

doi:10.1021/ol016243t

Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues

Org Lett. 2001 Aug 9;3(16):2575-8. doi: 10.1021/ol016243t.

Authors

M Kambe¹, E Arai, M Suzuki, H Tokuyama, T Fukuyama

Affiliation

¹ 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.

PMID: 11483064
DOI: 10.1021/ol016243t

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antibiotics, Antineoplastic / chemical synthesis*
Cross-Linking Reagents
Crystallography, X-Ray
Cyclization
Oxazines / chemical synthesis*
Stereoisomerism
Streptomyces / chemistry

Substances

Antibiotics, Antineoplastic
Cross-Linking Reagents
Oxazines
FR 900482