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Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan
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; in revised form: 16 April 2010 / Accepted: 19 April 2010 / Published: 21 April 2010
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
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MDPI and ACS Style
Wada, Y.; Fujioka, H.; Kita, Y. Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins. Mar. Drugs 2010, 8, 1394-1416.
Wada Y, Fujioka H, Kita Y. Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins. Marine Drugs. 2010; 8(4):1394-1416.
Wada, Yasufumi; Fujioka, Hiromichi; Kita, Yasuyuki. 2010. "Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins." Mar. Drugs 8, no. 4: 1394-1416.