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Synthesis 2007(5): 669-674
DOI: 10.1055/s-2007-965907
DOI: 10.1055/s-2007-965907
PAPER
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of Marine Bisindole Alkaloid (+)-cis-Dihydrohamacanthin B
Further Information
Received
20 October 2006
Publication Date:
25 January 2007 (online)
Publication History
Publication Date:
25 January 2007 (online)
Abstract
The total synthesis of the marine bisindole alkaloid (+)-cis-dihydrohamacanthin B was achieved from optically pure (R)-indolylglycinol.
Key words
bromoindole - indolylglycinol - oxazolidin-2-one - pyrazine - Staudinger reduction
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References
In the former synthesis of unnatural 2c from (S,R)-3, its diastereomer (R,R)-5 was also obtained. [6] So, we initially used (R,R)-5 for the approach to natural 2c.
8The catalytic hydrogenation (H2, Pd/BaSO4) of (R,R)-4 was also not successful.
12As described in the previous report, [6] there was no facial selectivity between E- and Z-isomers of 8 at the azidation step.
14The enantiomeric excess of 10 was determined by its HPLC compared with that of racemic sample.