First total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide

Authors
Kende, AS Hernando, JIM Milbank, JBJ
Citation
As. Kende et al., First total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide, ORG LETT, 3(16), 2001, pp. 2505-2508
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
16
Year of publication
2001
Pages
2505 - 2508
Database
ISI
SICI code
1523-7060(20010809)3:16<2505:FTSO(A>2.0.ZU;2-1
Abstract
[GRAPHICS] The total synthesis of the tetracyclic alkaloids stemonamide (1) and isoste monamide (2) is presented. The key step is the reaction between a silyloxyf uran and an N-acyliminium ion. The second quaternary center is created by a n intramolecular aldol spirocyclization. After 1,4-addition of an appropria te side chain, the methyl and double bond are installed by Mannich reaction . The seven-membered ring is closed by intramolecular nucleophilic displace ment.