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 |  |
| 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.
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| 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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