P-18 4-アルコキシ-2-トリメチルシロキシ-3-ブテンニトリル誘導体の反応と縮環状エーテル合成への応用(ポスター発表の部)

概要

論文の詳細を見る
Since trans-fused polycyclic ethers are often seen in potently bioactive natural products, such as ciguatoxin (1), they attract significant synthetic attention. So far, many approaches have been studied for their efficient construction. Among these approaches, a ring-closing olefin metathesis reaction (RCM) has now become one of the most reliable methods for the construction of medium-sized cyclic ethers. However, preparation of the precursors for RCM involves a serious difficulty of the stereoselective construction of their acyclic branched ether part. Therefore, we explored an efficient branched ether formation reaction. Here, BF_3・OEt_2 promoted site-selective reduction of 4-alkoxy-2-trimethylsilyloxy-3-butenenitrile (5), prepared through a process including intermolecular hetero-Michael reaction of a 2-butynoate ester derivative (3) with an alcohol (2), with R_3SiH or Bu_3SnH is disclosed, along with the efficient application to the synthesis of fused medium-ring ethers involving the EF-ring segment of CTX1B (1).
天然有機化合物討論会の論文
2005-09-15