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A Total Synthesis of Bifidenone.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2017 Apr 21; Vol. 82 (8), pp. 4235-4241. Date of Electronic Publication: 2017 Mar 31. - Publication Year :
- 2017
-
Abstract
- The first total synthesis of bifidenone, a novel natural tubulin polymerization inhibitor, has been achieved in 12 steps starting from commercially available 1,4-dioxaspiro[4.5]decan-8-one. The synthesis includes a newly developed method to generate the dihydrobenzodioxolone core by palladium-catalyzed aerobic dehydrogenation. The three stereocenters were installed with an AD-mix-β dihydroxylation step followed by a late-stage palladium-catalyzed decarboxylation-allylation procedure. The absolute stereochemistry of 3 was determined via 13a by single-crystal X-ray analysis.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 82
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 28351141
- Full Text :
- https://doi.org/10.1021/acs.joc.7b00202