A dirhodium(II)-carbenoid route to (-)- and (+)-Geissman-Waiss lactone: Synthesis of (1R,7R,8R)-(-)-turneforcidine

Authors
Wee, AGH
Citation
Agh. Wee, A dirhodium(II)-carbenoid route to (-)- and (+)-Geissman-Waiss lactone: Synthesis of (1R,7R,8R)-(-)-turneforcidine, J ORG CHEM, 66(25), 2001, pp. 8513-8517
Citations number
47
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
25
Year of publication
2001
Pages
8513 - 8517
Database
ISI
SICI code
0022-3263(200112)66:25<8513:ADRT(A>2.0.ZU;2-2
Abstract
(-)- and (+)-Geissman-Waiss lactone, 4b, was efficiently prepared via the i ntramolecular C-H insertion reaction of the chiral nonracemic diazoacetates (-)-5a and (+)-5b catalyzed by dirhodium(II) tetrakis[methyl (5R and 5S)-3 -phenylpropanoyl-2-imidazolidinone-5-carboxylate]. The cyclization was foun d to proceed with excellent regioselectivity and cis-diastereoselectivity. The bicyclic lactone (-)-4b was successfully used in the synthesis of the n ecine base, (-)-turneforcidine 2.