Application of an organozinc reagent derived from (S)-pyroglutamic acid: aformal synthesis of epibatidine

Authors
Karstens, WFJ Moolenaar, MJ Rutjes, FPJT Grabowska, U Speckamp, WN Hiemstra, H
Citation
Wfj. Karstens et al., Application of an organozinc reagent derived from (S)-pyroglutamic acid: aformal synthesis of epibatidine, TETRAHEDR L, 40(49), 1999, pp. 8629-8632
Citations number
52
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
49
Year of publication
1999
Pages
8629 - 8632
Database
ISI
SICI code
0040-4039(199912)40:49<8629:AOAORD>2.0.ZU;2-A
Abstract
A formal total synthesis of natural (-)-epibatidine has been developed. Key steps in the synthesis are a copper(I)-mediated coupling of an (S)-pyroglu tamic acid-derived organozine reagent with 1-iodo-3-trimethylsilyl-1-propyn e and an N-acyl- or N-sulfonyliminium ion cyclization, Following this route , various N-protected hydroxylactams were converted into 7-azabicylo[2,2,1] heptane derivatives, (C) 1999 Elsevier Science Ltd. All rights reserved.