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An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine

โœ Scribed by Stephen K. Taylor; Milica Ivanovic; Lloyd J. Simons; Matthew M. Davis

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
190 KB
Volume
14
Category
Article
ISSN
0957-4166

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โœฆ Synopsis

Efficient, formal syntheses of aphanorphine and eptazocine are reported that involve epoxide cyclizations. The necessary chiral epoxides were prepared following treatment of diols prepared by Sharpless asymmetric osmylations of an alkene. The cyclizations formed a ring compound with the same enantiomeric purity as the starting epoxide.

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Chemical asymmetric syntheses of the key intermediates (4,6,8) for the \_\_ synthesis of monobactam antibiotics ( SQ 26776 (azthreonam), sulfazecin, and SQ 26180 ) are accomplished from I\*)-4-phenylsulfonyl-2-azetidinone. Recently much attention have been focused on the nonclassical B-lactam antibi