Synthetic Studies toward Pseudolaric Acids: Radical Cyclization to Form Bridged Scaffold
Yujie Niu , Minggui Lin , Hao Cui , Yanji Huang , Yang Shen , Yandong Zhang
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (15) : 1699 -1705.
Synthetic Studies toward Pseudolaric Acids: Radical Cyclization to Form Bridged Scaffold
Pseudolaric acids are a family of diterpenoid natural products that exhibit a broad spectrum of biological activities. The main structural feature of their framework is a trans-fused perhydroazulene bearing a bridged lactone positioned at the junction of the rings. Herein, we have developed a radical cyclization strategy that allows flexible tuning of the cyclization process through diverse silicon substitutions on the substrates. This strategy can assist in constructing a series of skeletons with structural resemblance to pseudolaric acids and expedites the construction of the bridged lactone. Finally, it facilitates the synthesis of the entire skeletal structure of the pseudolaric acid family of natural products, excluding the B-ring functionalization.
Terpenoids / Total synthesis / Radical cyclization / Bridged cycles / Regioselectivity
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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