A facile synthesis of (-)- and (+)-Geissman-Waiss lactone via intramolecular Rh(II)-carbenoid mediated C-W insertion reaction: synthesis of (1R,7R,8R)-turneforcidine

Authors
Wee, AGH
Citation
Agh. Wee, A facile synthesis of (-)- and (+)-Geissman-Waiss lactone via intramolecular Rh(II)-carbenoid mediated C-W insertion reaction: synthesis of (1R,7R,8R)-turneforcidine, TETRAHEDR L, 41(47), 2000, pp. 9025-9029
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
47
Year of publication
2000
Pages
9025 - 9029
Database
ISI
SICI code
0040-4039(20001118)41:47<9025:AFSO(A>2.0.ZU;2-Y
Abstract
The intramolecular C-H insertion reaction in chiral non-racemic diazoacetat es (-)-6 and (+)-8 catalyzed by chiral Rh-2(MPPIM)(4) proceeded efficiently , with excellent regioselectivity and cis-diastereoselectivity, to give (-) - and (+)-Geissman-Waiss lactone, 4b, respectively. Bicyclic lactone (-)-4b was used in the synthesis of the necine base (-)-turneforcidine 3. (C) 200 0 Elsevier Science Ltd. All rights reserved.