A concise and efficient novel synthesis of cleviolide

Authors
Rossi, R Bellina, F Biagetti, M
Citation
R. Rossi et al., A concise and efficient novel synthesis of cleviolide, SYN COMMUN, 29(19), 1999, pp. 3415-3420
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
19
Year of publication
1999
Pages
3415 - 3420
Database
ISI
SICI code
0039-7911(1999)29:19<3415:ACAENS>2.0.ZU;2-#
Abstract
Cleviolide 1 has been synthesized in 73 % overall yield by a short reaction sequence involving the preparation of 4-methyl-1-trimethylsilylpent-3-en-1 -yne 7 from trimethylsilylethynylzinc chloride 6 and 1-bromo-2-methylpropen e 5, the direct conversion of 7 into the corresponding 1-tributylstannyl de rivative 8 and the Pd-catalysed reaction of this organotin derivative with 4-bromofuran-2(5H)-one 10.