Total synthesis of (+/-)-6-deoxycastanospermine: an application of the addition of organoboronates to N-acyliminium ions

Authors
Batey, RA MacKay, DB
Citation
Ra. Batey et Db. Mackay, Total synthesis of (+/-)-6-deoxycastanospermine: an application of the addition of organoboronates to N-acyliminium ions, TETRAHEDR L, 41(51), 2000, pp. 9935-9938
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
51
Year of publication
2000
Pages
9935 - 9938
Database
ISI
SICI code
0040-4039(200012)41:51<9935:TSO(AA>2.0.ZU;2-Y
Abstract
An efficient synthesis of (+/-)-6-deoxycastanospermine is reported, using a diastereoselective coupling of organoboronates with N-acyliminium ions as the key step. The construction of the indolizidine ring system is completed using a subsequent reductive amination reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.