96(P-53) 3-イソシアノテオネリンの短工程合成およびその類似体の付着阻害活性(ポスター発表の部)

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3-Isocyanotheonellin 1, isolated from a nudibranch, is a marine sesquiterpene of the bisabolene class with the characteristic nitrogen substituent at the C-3 position. In spite of its simple structure, this natural product exhibits potent antifouling activity against the larvae of the barnacle Balanus amphirite (EC_<50>0.13μg/mL). Efficient synthetic access to this natural product and various synthetic analogues will promote useful contributions of the antifouling field. For this reason, we planned a short total synthesis of 1 and the synthesis of its analogues. The structure-activity relationship with antifouling activity is discussed. The synthesis was started from 1,4-cyclohexanedione mono-ethyleneketal 5, which was converted into tert-alcohol 3 via sulfone 4 in five steps. The key step, the one-step construction of isocyao-sulfone 2 from tert-alcohol 3, was examined with TMSCN and silver salts. The most acceptable result on stereoselectivity was obtained when TMSCN and AgBF_4 were used in dichloromethane. Synthesis of 3-isocyanotheonellin 1 was accomplished by Julia olefination with isocyano-sulfone 2 and 4-methyl-2-pentenal as the final step. Geometrical isomer 10 was generated simultaneously. Isomers 11 and 12 were obtained by the same route from isocyano-sulfone 9. Moreover, the antifouling activity of 1, 10, 11, and 12 was measured and is discussed in terms of the structure-activity relationship.
天然有機化合物討論会の論文
2001-09-01

96(P-53) 3-イソシアノテオネリンの短工程合成およびその類似体の付着阻害活性(ポスター発表の部)

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