Total Synthesis of Marine Bisindole Alkaloid (+)-cis-Dihydrohamacanthin B

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

References

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7

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.

8

The catalytic hydrogenation (H₂, Pd/BaSO₄) of (R,R)-4 was also not successful.

12

As described in the previous report, [6] there was no facial selectivity between E- and Z-isomers of 8 at the azidation step.

14

The enantiomeric excess of 10 was determined by its HPLC compared with that of racemic sample.