CONJUGATE ADDITION OF A CYANO-GILMAN CUPRATE TO AN ACRYLIC-ACID - HOMOLOGATION OF ARTEMISINIC ACID AND SUBSEQUENT CONVERSION TO 16-BUTYLARTEMISININ

Authors
VROMAN JA ELSOHLY HN AVERY MA
Citation
Ja. Vroman et al., CONJUGATE ADDITION OF A CYANO-GILMAN CUPRATE TO AN ACRYLIC-ACID - HOMOLOGATION OF ARTEMISINIC ACID AND SUBSEQUENT CONVERSION TO 16-BUTYLARTEMISININ, Synthetic communications, 28(9), 1998, pp. 1555-1562
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
28
Issue
9
Year of publication
1998
Pages
1555 - 1562
Database
ISI
SICI code
0039-7911(1998)28:9<1555:CAOACC>2.0.ZU;2-V
Abstract
Conjugate addition to the acrylic acid moiety of artemisinic acid 2 wa s made possible by in situ protection as a silyl ester, treatment with a cyano-Gilman cuprate [Bu2CuLi . LiCN] to facilitate 1,4-addition, a nd deprotective workup affording the homologated carboxylic acid 9. Ph otoxygenation and acid treatment of 9 then led to the facile preparati on of potent antimalarial 9-modified analogs of artemisinin.