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Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B
Yunxia Yang1, Dong Xie1, Liang Huo1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, Gansu, PR China.
Abstract:
Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction. This synthesis establishes a concise asymmetric approach to access artatrovirenols A and B, and also provides insightful evidence to their biogenetic pathway in nature.
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