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Synfacts 2023; 19(11): 1065
DOI: 10.1055/s-0042-1752234
Synthesis of Natural Products

Total Synthesis of (±)-iso-Phomopsene

Authors

    Rezensent(en):

  • Erick M. Carreira

  • Willi M. Amberg

Yin J.-J, Wang Y.-P, Xue J, Zhou F.-F, Shan X.-Q, Zhu R, Fang K, Shi L, *, Zhang S.-Y, Hou S.-H, *, Xia W, Tu Y.-Q. * Harbin Institute of Technology, Shanghai Jiao Tong University and Lanzhou University, P. R. of China
Total Syntheses of Polycyclic Diterpenes Phomopsene, Methyl Phomopsenonate, and iso-Phomopsene via Reorganization of C–C Single Bonds.

J. Am. Chem. Soc. 2023;
145: 21170-21175
DOI: 10.1021/jacs.3c07044
CrossrefPubMedSuche in Google Scholar
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Key words

(±)-iso-phomopsene - diterpenoid - Ghosez cycloaddition - Knoevenagel condensation - Nazarov cyclization - Wagner–Meerwein rearrangement - Krapcho decarboxylation - Rubottom oxidation - Beckmann fragmentation - carbonyl–ene cyclization - Dess–Martin oxidation - Kumada coupling

Significance

Shi, Hou, Tu and co-workers report the total synthesis of phomopsene, methyl phomopsenonate, and iso-phomopsene. These natural products feature a 5/5/6/5 tetracyclic skeleton. The authors revised the structure of iso-phomopsene in this work.


 

Comment

Key to success is an InCl3-catalyzed Nazarov cyclization of dicyclobutane K followed by Wagner–Meerwein rearrangements to afford tetracycle M. Ring expansion via Beckmann fragmentation completed the carbocyclic framework.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
14. Oktober 2023

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