A NEW SYNTHETIC METHOD FOR ALLENE-1,3-DICARBOXYLATES USING DMC AND A NOVEL TANDEM CYCLIZATION TO A PYRROLIZIDINE ALKALOID SKELETON

Authors
NODE M FUJIWARA T ICHIHASHI S NISHIDE K
Citation
M. Node et al., A NEW SYNTHETIC METHOD FOR ALLENE-1,3-DICARBOXYLATES USING DMC AND A NOVEL TANDEM CYCLIZATION TO A PYRROLIZIDINE ALKALOID SKELETON, Tetrahedron letters, 39(35), 1998, pp. 6331-6334
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
35
Year of publication
1998
Pages
6331 - 6334
Database
ISI
SICI code
0040-4039(1998)39:35<6331:ANSMFA>2.0.ZU;2-G
Abstract
A new one-step synthesis of allene-1,3-dicarboxylates from acetone-1,3 -dicarboxylates in high yields was developed by the use of DMC as a de hydrating reagent. This process opened a new expeditious route to a 1- azabicyclo[3.3.0]octane skeleton of pyrrolizidine alkaloids from dimet hyl acetone-1,3-dicarboxylate and bis(2-chloroethyl)amine via a Michae l addition and a novel tandem cyclization. (C) 1998 Elsevier Science L td. All rights reserved.