Axinella cannabina axisothiocyanate 4 from

Axisonitrile-1 (1) and axisothiocyanate-1 (2) were the first pair of NC/NCS compounds isolated from Axinella cannabina, see Introduction [1]. That both compounds possessed a new skeleton was evident, when 1 was reduced (Li/EtNH2) to axane (6). Other transformations involving the exocyclic methylene which survived selective reduction (Na/NH3) of 1, coupled with evaluation of the lHNMR data, supported its gross structure. Confirmation of 2 was secured when 1 was heated with sulfur and the resultant purified product found to be identical to the natural product. 

Cafieri, F., Fattomsso, E., Magno, S., Santacroce, C., and Sica, D. (1973) Isolation and stmcture of axisonitrile and axisothiocyanate two unusual sesquiterpenoids from the marine sponge Axinella cannabina. Tetrahedron, 29, 4259-4262. 

Cafieri, F., E. Fattorusso, S. Magno, C. Santacroce, and D. Sica Isolation and Structure of Axisonitrile-1 and Axisothiocyanate-1, two unusual Sesquiterpenoids from the marine sponge Axinella cannabina. Tetrahedron 29, 4259 (1973). 

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