AbstractScabrolide A is a norditerpenoid derived from soft coral and is considered a promising natural product as a seed compound for novel anti-Chikungunya virus drugs. Structurally, it possesses a unique tetracyclic framework composed of 5/6/7-membered rings and a γ-lactone, along with five consecutive stereogenic centers. Due to these features, the total synthesis of scabrolide A presents a significant challenge from both biological and organic synthetic chemistry perspectives.We have embarked on the asymmetric total synthesis of scabrolide A by designing an innovative synthetic strategy that allows the rapid construction of its fused ring system from a macrocyclic intermediate in the final stages of synthesis.To date, we have successfully linked a five-membered vinyl iodide to another asymmetrically synthesized fragment. In addition, regio- and stereoselective functional group modifications on the five-membered ring have been completed, and we have synthesized the key intermediate via an 11-step longest linear sequence.はじめに目的：抗チクングニアウイルス (CHIKV) 活性を示す稀少海洋産ノルジテルペン類の網羅的で効率的な全合成戦略を確立し，天然物創薬研究に有機合成化学の立場から貢献することを目指す．具体的には，生合成経路の終点に位置する縮環系ヨナラン類スカブロリド A (1) から生合成経路を「逆」にたどる革新的な合成戦略を用いて，生合成経路の上流に位置する非縮環系大環状ノルセンブラノイド類をも網羅的に全合成する．北海道大学大学院薬学研究院天然物合成化学研究室・教授長友 優典Hokkaido UniversityMasanori Nagatomo― 88 ―生合成経路を「逆」に辿る稀少海洋産ノルジテルペン類の網羅的全合成Unified total synthesis of marine norditerpenes enabled by the synthetic strategy reversed from biosynthesis
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