(+)-Bruguierol C
October 10th, 2007 by Natural Product
Today, some interesting target – (+)-Bruguierol C:
This natural product was first isolated in 2005 from the stem of Bruguiera gymmorrhiza mangrove tree. Bruguierol C has interesting biological properties – for example exhibits modest antimicrobial activities (probably because of meta hydroxy substituted aromatic ring) including antimicrobial activity aganist Enterococcus faecalis (which shows resistance to popular antibiotics).
Retrosynthetic analysis is shown below:
The key simplification is first conversion – intramolecular Friedel-Crafts reaction depending on capture of in situ generated oxocarbenium cation.
Complete synthesis is drawn below:
Reduction of starting ester with DIBAL directly to aldehyde wasn’t selective so team decided to use LiAlH4 and they oxidized formed alcohol in next step. Also, utilizing of TPAP (tetra-n-propylammonium perruthenate) in lactonization is interesting.
For more information see:
D. M. Solorio, M. P. Jennings, J. Org. Chem., 2007, 72, 6621.
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March 29th, 2008 at 7:25 pm
[...] cyclization, ring expansion (with use diazo compound) and TPAP-promoted cyclization (see also Total Synthesis of Bruguierol C for other application of that key reaction). I’m waiting for your [...]
May 13th, 2008 at 5:09 pm
[...] stem of bruguiera gymmorrhiza mangrove tree. Bruguierol C has interesting biological properties – fohttp://www.totalsynthesis.eu/2007/10/10/total-synthesis-of-bruguierol/Bruguiera gymnorrhizaThousands of tons of bruguiera wood chips are exported annually from Indonesia, [...]