Synthesis of oxazolidinyl azacycles via ring-closing olefin metathesis: a practical entry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines

Authors
Subramanian, T Lin, CC Lin, CC
Citation
T. Subramanian et al., Synthesis of oxazolidinyl azacycles via ring-closing olefin metathesis: a practical entry to the synthesis of deoxy-azasugars and hydroxypyrrolizidines, TETRAHEDR L, 42(24), 2001, pp. 4079-4082
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
24
Year of publication
2001
Pages
4079 - 4082
Database
ISI
SICI code
0040-4039(20010611)42:24<4079:SOOAVR>2.0.ZU;2-#
Abstract
Starting with D- and L-serines, an expedient method for the preparation of oxazolidinyl piperidines, azepenes and azacyclooctenes was illustrated as a route to various deoxy-azasugars and hydroxypyrrolizidines. The ring-closi ng olefin metathesis of oxazolidinyl di-olefins was used as a key-step to c onstruct the azacycles. Consecutive epoxidation, hydrolysis and transannula tion of oxazolidinyl azacyclooctene led to hydroxypyrrolizidines. (C) 2001 Elsevier Science Ltd. All rights reserved.