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Mar. Drugs 2010, 8(4), 1394-1416; doi:10.3390/md8041394
Review

Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins

1,, 1,*  and 1,*
1 Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan 2 College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan JSPS Research Fellow.
* Authors to whom correspondence should be addressed.
Received: 7 April 2010 / Revised: 16 April 2010 / Accepted: 19 April 2010 / Published: 21 April 2010
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges)

Abstract

Manynatural products with biologically interesting structures have been isolated from marine animals and plants such as sponges, corals, worms, etc. Some of them are discorhabdin alkaloids. The discorhabdin alkaloids (discorhabdin A-X), isolated from marine sponges, have a unique structure with azacarbocyclic spirocyclohexanone and pyrroloiminoquinone units. Due to their prominent potent antitumor activity, discorhabdins have attracted considerable attention. Many studies have been reported toward the synthesis of discorhabdins. We have accomplished the first total synthesis of discorhabdin A (1), having the strongest activity in vitro among discorhabdins in 2003. In 2009, we have also accomplished the first total synthesis of prianosin B (2), having the 16,17-dehydropyrroloiminoquinone moiety, by a novel dehydrogenation reaction with a catalytic amount of NaN3. These synthetic studies, as well as syntheses of the discorhabdins by various chemists to-date, are reviewed here.
Keywords: discorhabdin alkaloid; marine sponge; cytotoxic activity discorhabdin alkaloid; marine sponge; cytotoxic activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Wada, Y.; Fujioka, H.; Kita, Y. Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins. Mar. Drugs 2010, 8, 1394-1416.

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