Bioinspired Total Syntheses of Gymnothelignans

Abstract

Since 2012, Xu and Zhou have reported the isolation of a series of gymnotheligans, a large group of novel tetrahydrofuran-containing lignan natural products. In the past decade, considerable achievements in the total syntheses of these lignans have been achieved based on a plausible biogenetic pathway proposed by our group in 2014. In this account, we summarize these remarkable synthetic works of the past ten years.

1 Introduction

2 Biogenetic Pathways to Gymnothelignans

3 Total Syntheses of Eupodienones

4 Total Syntheses of Eupomatilones

5 Total Synthesis of Dibenzocyclooctenes

6 Conclusions

Key words

total synthesis - biogenetic pathway - gymnothelignans - eupodienone - eupomatilone - dibenzocyclooctene

• References

• 1a Apers S, Vlietinck A, Pieters L. Phytochem. Rev. 2003; 2: 201
• 1b Lee K.-H, Xiao Z. Phytochem. Rev. 2003; 2: 341
• 1c Westcott ND, Muir AD. Phytochem. Rev. 2003; 2: 401
• 1d Saleem M, Kim HJ, Ali MS, Lee YS. Nat. Prod. Rep. 2005; 22: 696
• 1e Pan J.-Y, Chen S.-L, Yang M.-H, Wu J, Sinkkonen J, Zou K. Nat. Prod. Rep. 2009; 26: 1251
• 1f Zhuang T, Li F, Huang L.-R, Liang J.-Y, Qu W. Chem. Biodivers. 2015; 12: 194
• 2a He D, Ding L, Xu H, Lei X, Xiao H, Zhou Y. J. Org. Chem. 2012; 77: 8435
• 2b Xiao S, He D, Fang D, Chen F, Ding L, Zhou Y. Helv. Chim. Acta 2014; 97: 499
• 2c Xiao S.-J, Chen F, Ding L.-S, Zhou Y. Chin. Chem. Lett. 2014; 25: 463
• 2d Xiao S.-J, Lao Y.-Z, Chen F, Xu H.-X, Ding L.-S, Zhou Y. Phytochem. Lett. 2014; 8: 38
• 2e Xiao S.-J, Zhang M.-S, Guo D.-L, Chen F, Zhou Y, Ding L.-S. Chin. Chem. Lett. 2017; 28: 1049
• 2f Majdecki M, Niedbała P, Jurczak J. ChemistrySelect 2020; 5: 6424
• 2g Majdecki M, Tyszka-Gumkowska A, Jurczak J. Org. Lett. 2020; 22: 8687
• 2h Majdecki M, Grodek P, Jurczak J. J. Org. Chem. 2021; 86: 995
• 2i Zhang Y.-M, Su M.-S, Shao F, Yang M, Zhang P.-Z. Chem. Nat. Compd. 2018; 54: 1118
• 2j Lu D.-W, Zhang X, Chen M.-H. Chem. Nat. Compd. 2022; 58: 411
• 3 Li H, Zhang Y, Xie X, Ma H, Zhao C, Zhao G, She X. Org. Lett. 2014; 16: 4440
• 4 Choi H, Choi J, Han J, Lee K. J. Org. Chem. 2022; 87: 4316
• 5 Guérard KC, Sabot C, Beaulieu M.-A, Giroux M.-A, Canesi S. Tetrahedron. 2010; 66: 5893
• 6 Choi H, Jang H, Kim H, Lee K. Org. Lett. 2019; 21: 7857
• 7 Han J, Choi H, Choi J, Lee K. Org. Lett. 2022; 24: 2926
• 8a Chaimanee S, Pohmakotr M, Kuhakarn C, Reutrakul V, Soorukram D. Org. Biomol. Chem. 2017; 15: 3985
• 8b Soorukram D, Pohmakotr M, Kuhakarn C, Reutrakul V. J. Org. Chem. 2018; 83: 4173
• 9 Chen P, Huo L, Li H, Liu L, Yuan Z, Zhang H, Feng S, Xie X, Wang X, She X. Org. Chem. Front. 2018; 5: 1124