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Elucidation of spirodactylone, a polycyclic alkaloid from the sponge Dactylia sp., and nonenzymatic generation from the co-metabolite Denigrin B
Kang, U.; Caldwell, D.R.; Cartner, L.K.; Wang, D.; Kim, C.-K.; Tian, X.; Bokesch, H.R.; Henrich, C.J.; Woldemichael, G.M.; Schnermann, M.J.; Gustafson, K.R. (2019). Elucidation of spirodactylone, a polycyclic alkaloid from the sponge Dactylia sp., and nonenzymatic generation from the co-metabolite Denigrin B. Organic Letters 21(12): 4750-4753. https://dx.doi.org/10.1021/acs.orglett.9b01636
In: Organic Letters. AMER CHEMICAL SOC: Washington. ISSN 1523-7060; e-ISSN 1523-7052, more
Peer reviewed article  

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Keyword
    Marine/Coastal

Authors  Top 
  • Kang, U.
  • Caldwell, D.R.
  • Cartner, L.K.
  • Wang, D., more
  • Kim, C.-K.
  • Tian, X.
  • Bokesch, H.R.
  • Henrich, C.J.
  • Woldemichael, G.M.
  • Schnermann, M.J.
  • Gustafson, K.R.

Abstract
    Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1). This confirmed the assigned structure and provides insight into the probable biogenesis of 1.

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