101(P24) 新規アルカロイドTAN1251Aの全合成研究(ポスター発表の部)
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Novel-type alkaloids, TAN1251 A, B, C and D, were isolated from a culture of Penicillium thomii RA-89 by the research group of Takeda Chemical Industries Ltd. The structures involve a unique tricyclic skeleton which consists of a 1,4-diazabicyclo[3,2,1]octane ring and a cyclohexanone ring through a spiro bond. The skeleton is linked to a long side chain through a Z-double bond. The compounds have been found to show cholinergic activity on the basis of the radio ligand receptor binding assay by using 3H-quinuclidinyl benzilate (QNB) and microsomal fractions of rat cerebral cortex. Especially, the affinity of TAN1251B to a muscarinic acetylcholine receptor is stronger than that of atropine. TAN1251A was selective to the M1 subtype of muscarinic receptor. Such structural complexity and interesting biological activity provided us the stimulus for elaborating the synthetic study of TAN1251 derivatives. We wish to report here the first total synthesis of racemic TAN1251A and the formal asymmetric synthesis of the compound.
- 天然有機化合物討論会の論文
- 1998-08-31
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