25 (±)-Coriolinの全合成

概要

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A total synthesis of (±)-coriolin, an antibacterial and antitumor sesquiterpenoid, has been accomplished starting from 1,3-cyclooctadiene. (1) Synthesis of the enone (1), a versatile intermediate The enone (1) was successfully contructed from the simple alcohol (2) by two routes. One of the routes involving regio and stereo-controlled bromohydrin formation (7) was found to be applicable to practical scale synthesis of 1. (2) Introduction of functional groups to the enone (1) A conjugate addition of dimethylcopperlithium to the enone (1) afforded the methyl ketone (11) in high yield, which was followed by regiospecific alkylation and reduction of a carbonyl group to provide the alcohol (13) efficiently. (3) Synthesis of (±)-coriolin The alcohol (13) was converted to (±)-coriolin in 13 steps. Introduction of an acetonyl group (18) and a hydroxy group (27) in the regio and stereocontrolled manner is a characteristic point. The present total synthesis would be easily applicable to synthesis of various coriolin analogs. (4) Synthesis of the prostacyclin analog (29) In order to point out versatility of the key intermediate (1), application to synthesis of the prostacyclin analog (29) is briefly presented. Application of the present synthesis to asymmetric synthesis including asymmetric epoxidation of 1,3-cyclooctadiene is currently under investigation.
天然有機化合物討論会の論文
1980-09-10