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. 2008 Mar;9(3):401-421.
doi: 10.3390/ijms9030401. Epub 2008 Mar 24.

Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare

Yoshihide Usami  1 , Hayato Ichikawa  1 , Masao Arimoto  1
Affiliations

Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare

Yoshihide Usami et al. Int J Mol Sci. 2008 Mar.

Abstract

Pericosines are unique C(7) cyclohexenoid metabolites of Periconia byssoides OUPS-N133 fungus that was originally isolated from the sea hare, Aplysia kurodai. Pericosines show significant in vitro cytotoxicity against P388 lymphocytic leukemia cells. Pericosine A, in particular, shows the most potent activity and significant in vivo antitumor activity against P388 cells. Thus, pericosines are promising candidates for seed compounds of anticancer drugs. However, before the total syntheses of pericosines were accomplished, their stereo structures could not be determined by spectral analyses because they have multi-functionalized cyclohexenoid structures with torsional strain. In this review, synthetic efforts for pericosines in this decade are surveyed.

Keywords: antitumor; carbasugar; marine natural product; pericosine; structure determination; total synthesis.

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Figures

Figure 1.
Figure 1.
Structures of bioactive carbasugars as synthetic targets.
Figure 2.
Figure 2.
Structures of pericosines and analogues.
Figure 3.
Figure 3.
Comparison of coupling constants between epimer of pericosine B 7 and pericosine A 1.
Figure 4.
Figure 4.
Coupling constants in Hz observed in 1H-NMR spectra of pericosines and their analogues.
Scheme 1.
Scheme 1.
Successful total synthesis of (+)-pericosine B by Donohoe and co-workers.
Scheme 2.
Scheme 2.
Okamura’s approach.
Scheme 3.
Scheme 3.
Usami’s approach.
Scheme 4.
Scheme 4.
Garcia Ruano’s approach involving asymmetric Diels-Alder cycloaddition.
Scheme 5.
Scheme 5.
Synthesis of epimer of pericosine B from (−)-quinic acid.
Scheme 6.
Scheme 6.
Retro-synthetic strategy of 6 and 9.
Scheme 7.
Scheme 7.
Total synthesis of initially assigned pericosine A 6.
Scheme 8.
Scheme 8.
Synthesis of initially assigned pericosine D 9.
Scheme 9.
Scheme 9.
First total synthesis of (−)-pericosine A 1 from (−)-shikimic acid.
Scheme 10.
Scheme 10.
Total synthesis of (+)-pericosine A from (−)-quinic acid.
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References

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