Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

Xie, Sujun; Chen, Yuye; Zhang, Yan; Zhang, Zhiting; Hu, Xinyue; Yan, Chongyuan; Xu, Jing

doi:10.1016/j.xcrp.2024.101855

Cell Reports Physical Science

2024

DOI: 10.1016/j.xcrp.2024.101855

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Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

Sujun Xie,

Yuye Chen,

Yan Zhang

et al.

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2024

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Cited by 2 publications

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Total Synthesis of (+)‐Kalmanol

Ma,

et al. 2024

Angewandte Chemie

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Kalmanol, the flagship member of the kalmane diterpene family, possesses a complex and highly oxidized 5/5/8/5 tetracyclic skeleton with nine contiguous stereocenters and exhibits significant analgesic effects and cardiotoxic properties. We have achieved the efficient total synthesis of (+)‐kalmanol in 22 steps with 2.3% yield. The synthesis featured a Rh‐catalyzed [5+2+1] cycloaddition reaction to construct 5/5/8 tricyclic skeleton, and a meticulously designed sequence of stereoselective oxidations of the 5/5/8/5 tetracyclic skeleton.

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Total Synthesis of (+)‐Kalmanol

Ma,

et al. 2024

Angewandte Chemie

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Total Synthesis of (+)‐Kalmanol

Ma,

et al. 2024

Angew Chem Int Ed

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Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

Cited by 2 publications

References 138 publications

Total Synthesis of (+)‐Kalmanol

Total Synthesis of (+)‐Kalmanol

Total Synthesis of (+)‐Kalmanol

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