Total synthesis of coraxeniolide-A

Authors
Renneberg, D Pfander, H Leumann, CJ
Citation
D. Renneberg et al., Total synthesis of coraxeniolide-A, J ORG CHEM, 65(26), 2000, pp. 9069-9079
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
26
Year of publication
2000
Pages
9069 - 9079
Database
ISI
SICI code
0022-3263(200012)65:26<9069:TSOC>2.0.ZU;2-3
Abstract
The first total synthesis of optically active coraxeniolide-A (la) and 4-ep i-coraxeniolide-A (1b) is described. The approach is highly stereoselective and flexible in the preparation of a wide variety of members of the xeniol ide family. The use of the Grob-fragmentation was pivotal for the stereospe cific elaboration of the nine-membered ring. Coraxeniolide-A (la) was synth esized in 28 steps by using the Hajos-Parrish diketone 2 as starting materi al which is available enantiomerically pure.