多様な環状骨格構築法の開発と生物活性天然物合成への応用

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In this article, the author outlines five total syntheses of structurally unique and biologically intriguing natural products, which were matters of attractive concern in the author’s group during these two decades. The following natural product syntheses are summarized in this article: (1) a mycotoxin, (+)-asteltoxin, (2) sex-attracting insect pheromones, (−)-anastrephin and (−)-epianastrephin, (3) a bisabolene-type sesquiterpenoid, (+)-paniculide B, (4) 17-memberd tetra- and pentacyclic antibiotics, (+)-macquarimicins, and (5) cytotoxic and immunosuppressive caryophyllene-type sesquiterpenoid, (+)-pestalotiopsin A and its (−)-enantiomer. In conjunction with these total syntheses, the multigram-scale access to two versatile and enantiomerically homogeneous building blocks from D-glucose is also described. The synthetic utility of the both building blocks was convincingly demonstrated through the total syntheses of the above three natural products.