Spongian diterpenoids

Miyamoto, T., Sakamoto, K., Arao, K, Komori, T., Higuchi, R., and Sasaki, T., Dorisenones, cytotoxic spongian diterpenoids, from the nudibranch Chromodoris obsoleta, Tetrahedron, 52, 8187, 1996. 

Keyzers RA, Northcote PT, Davies-Coleman MT. Spongian diterpenoids from marine sponges. Nat. Prod. Rep. 2006 23 321-334. 

Cu-Bisoxazoline-catalyzed asymmetric cyclopropanation of methyl 2-furoate with ethyl diazoacetate was a key step in the synthesis of the cw-fused 5-oxofuro[23-fc]furan core of spongiane diterpenoids <05OL5353>. An interesting example of rtiodium-catalyzed intramolecular addition of a diazoketone to furan affording a strained cyclobutenone, is illustrated below. Iodine-induced isomerization of the product provided the fused tricyclic dihydrofuran compound <05HCA33Q>. 

Spongian diterpenoids from marine sponges. Keyzers, R.A., Northcote, P.T., Davies-Coleman, M.T. (2006), 23, 321-334. 

Gonzalez, M.A. (2007) Spongiane diterpenoids. Curr. Bioactive Comp., 3, 1-36. 

Gimasekera, S.P. and Schmitz, F.J. (1991) New spongian diterpenoids from a Great Barrier Reef sponge, Spongio sp. J. Org. Chem., 56, 1250-1253. 

Poiner, A. and Taylor, W.C. (1990) The constituents of marine sponges. IV. The isolation of degraded spongian diterpenoids from Aplysilla tango (sp. nov.) (Dendroceratida). Aust.J. Chem., 43,1713-1727. 

Fontana, A., MoHo, E., Ricdardi, D., Fakhr, L, and Cimino, G. (1997) Chemical studies of Egyptian opisthobranchs spongian diterpenoids from Glossodoris atromarpnata. J. Nat. Prod., 60, 444-448. 

Abad, A., Arno, M., Marin, M.L., and Zaragoza, R.J. (1991) First synthetic approach to spongian pentacycUc diterpenoids. Enantioselective synthesis of dendrillol-1. Synlett, 789-791. 

Abad, A., Agullo, C., Cunat, A.C., and Garcia, A.B. (2002) Synthesis of oxygenated spongiane-type diterpenoids from carvone. Tetrahedron Lett, 43, 7933-7936. 

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