TOTAL SYNTHESIS OF THE CYCLOPEPTIDE ALKALOID SANJOININE G1 AND ITS C-11 EPIMER

Authors
EAST SP SHAO F WILLIAMS L JOULLIE MM
Citation
Sp. East et al., TOTAL SYNTHESIS OF THE CYCLOPEPTIDE ALKALOID SANJOININE G1 AND ITS C-11 EPIMER, Tetrahedron, 54(44), 1998, pp. 13371-13390
Citations number
47
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
44
Year of publication
1998
Pages
13371 - 13390
Database
ISI
SICI code
0040-4020(1998)54:44<13371:TSOTCA>2.0.ZU;2-#
Abstract
The naturally occurring cyclopeptide alkaloid sanjoinine G1 and its C- 11 epimer were synthesized in 18 steps from D-serine. The key steps in the synthesis were the formation of the alkylaryl ether linkage via a ll SNAr reaction with 4-fluorobenzonitrile and the macrocyclization to form the 14-membered ring using a modification of the Schmidt protoco l involving an activated pentafluorophenyl ester. (C) 1998 Elsevier Sc ience Ltd. All rights reserved.