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A Total Synthesis of Bifidenone.

Authors :
Huang Z
Williams RB
O'Neil-Johnson M
Eldridge GR
Mangette JE
Starks CM
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