RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2024; 35(05): 543-551
DOI: 10.1055/a-2021-7993
DOI: 10.1055/a-2021-7993
account
Biomimetic Synthesis
Investigations on Biomimetic Dimerization in Natural Product Synthesis
We are grateful for financial support from the National Natural Science Foundation of China (22071192, 21772153) and the Shaanxi Provincial Science and Technology Department (2019JM-151).
Abstract
Biomimetic dimerization is a fascinating pathway to natural product synthesis. By using structurally inferior monomers, complex molecular architectures can be readily established with distinct efficiency and elegance. In this Account, our investigation on biomimetic dimerization in natural product synthesis has been summarized, which includes our synthetic exploration of linderaspirone A, bi-linderone, parvistemin A, (±)-diperezone, scabellone B, and spiroxins A/C/D.
1 Introduction
2 Biomimetic Dimerization in the Synthesis of Linderaspirone A and Bi-linderone
3 Biomimetic Dimerization in the Synthesis of Parvistemin A and (±)-Diperezone
4 Biomimetic Dimerization in the Synthesis of Scabellone B
5 Dimerization Investigation in the Synthesis of Spiroxins A/C/D
6 Conclusion
Key words
biomimetic synthesis - bioactivity - dimerization - natural product - biosynthetic proposal - oxidative coupling - oxo-6π electrocyclizationPublikationsverlauf
Eingereicht: 07. Dezember 2022
Angenommen nach Revision: 28. Januar 2023
Accepted Manuscript online:
28. Januar 2023
Artikel online veröffentlicht:
28. Februar 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Bentley R, Bennett JW. Annu. Rev. Microbiol. 1999; 53: 411
- 1b Scholz U, Winterfeldt E. Nat. Prod. Rep. 2000; 17: 349
- 1c Yoder RA, Johnston JN. Chem. Rev. 2005; 105: 4730
- 1d Brunoldi E, Luparia M, Porta A, Zanoni G, Vidari G. Curr. Org. Chem. 2006; 10: 2259
- 1e Bulger PG, Bagal SK, Marquez R. Nat. Prod. Rep. 2008; 25: 254
- 1f Kishimo S, Tsunematsu Y, Sato M, Watanabe K. Chem. Rec. 2017; 17: 1095
- 1g Caprioglio D, Salamone S, Pollastro F, Minassi A. Plants 2021; 10: 677
- 1h Bao R, Zhang H, Tang Y. Acc. Chem. Res. 2021; 54: 3720
- 1i Jamieson CS, Misa J, Tang Y, Billingsley JM. Chem. Soc. Rev. 2021; 50: 6950
- 1j Zhao Y, Long X, Wu H, Deng J. Org. Chem. Front. 2022; 9: 6979
- 1k Liu J, Xi S, Tang Y. Synlett 2022; 33: 836
- 3a Zhan Z, Ying Y, Ma L, Shan W. Nat. Prod. Rep. 2011; 28: 594
- 3b Stanley PA, Spiteri C, Moore JC, Barrow AS, Sharma P, Moses JE. Curr. Pharm. Des. 2016; 22: 1628
- 3c Han S, Jeon S, Park J. Synlett 2017; 28: 2353
- 3d Lombe BK, Feineis D, Bringmann G. Nat. Prod. Rep. 2019; 36: 1513
- 3e Sun J, Yang H, Tang W. J. Chem. Soc. Rev. 2021; 50: 2320
- 3f Chang Y, Sun C, Wang C, Huo X, Zhao W, Ma X. Nat. Prod. Rep. 2022; 39: 2030
- 4a Wang F, Gao Y, Zhang L, Liu JK. Org. Lett. 2010; 12: 2354
- 4b Wang F, Gao Y, Zhang L, Bai B, Hu Y, Dong Z, Zhai Q, Zhu H, Liu J. Org. Lett. 2010; 12: 3196
- 5 Tan H, Zheng C, Liu Z, Wang D. Org. Lett. 2011; 13: 2192
- 6 Wang G, Wei K, Zhang L, Feng T, Wang F, Wang A, Liu K. Tetrahedron Lett. 2011; 52: 2719
- 7a Xiao F, Liu W, Wang Y, Zhang Q, Li X, Hu X. Asian J. Org. Chem. 2013; 2: 216
- 7b Liu W, Xiao F, Hu X. Chin. J. Org. Chem. 2013; 33: 1587
- 7c Gai S, Zhang Q, Hu X. J. Org. Chem. 2014; 79: 2111
- 7d Li Q, Xiao F, Wang Y, Hu X. Synth. Commun. 2016; 46: 1062
- 8a Snyder SA, Kontes F. Isr. J. Chem. 2011; 51: 378
- 8b Wan C, Deng J, Liu H, Bian M, Li A. Sci. China: Chem. 2014; 57: 926
- 8c Liu B, Fu S, Zhou C. Nat. Prod. Rep. 2020; 37: 1627
- 9 Xiao F, Zhang Q, Wang Y, Huang X. Synthesis 2015; 47: 2545
- 10 Gao S, Hu X. Org. Chem. Front. 2017; 4: 1493
- 11 Yang X, Gulder TA. M, Reichert M, Tang CP, Ke C, Ye Y, Bringmann G. Tetrahedron Lett. 2007; 63: 4688
- 12 Joseph-Nathan P, Hernández JD, Román LU, Garcia EG, Mendoza V, Mendoza S. Phytochemistry 1982; 21: 1129
- 13 Georgantea P, Ioannou E, Vagias C, Roussis V. Tetrahedron Lett. 2013; 54: 6920
- 14 Smith MJ, Nawrat CC, Moody CJ. Org. Lett. 2011; 13: 3396
- 15 Sánchez I, Yáñez HR, Enríquez R, Joseph-Nathan P. J. Org. Chem. 1981; 46: 2818
-
16a
Moore HW,
Decker OH. W.
Chem. Rev. 1986; 86: 821
- 16b Perri ST, Foland SD, Decker OH. W, Moore HW. J. Org. Chem. 1986; 51: 3067
- 16c Heileman MJ, Tiedemann R, Moore HW. J. Am. Chem. Soc. 1998; 120: 3801
- 16d Hergueta AR, Moore HW. J. Org. Chem. 2002; 67: 1388
- 17a Liebeskind LS, Iyer S, Jewell CF. J. Org. Chem. 1986; 51: 3065
- 17b Liebeskind LS, Fengl RW, Wirtz KR, Shawe TT. J. Org. Chem. 1988; 53: 2482
- 17c Liebeskind LS. Tetrahedron Lett. 1989; 45: 3053
- 17d Shi X, Amin SR, Liebeskind LS. J. Org. Chem. 2000; 65: 1650
- 18 Chan ST. S, Pearce AN, Januario AH, Page MJ, Kaiser M, McLaughlin RJ, Harper JL, Webb VL, Barker D, Copp BR. J. Org. Chem. 2011; 76: 9151
- 19 Chan ST. S, Pullar MA, Khalil IM, Allouche E, Barker D, Copp BR. Tetrahedron Lett. 2015; 56: 1486
- 20 Yu T, Shu X, Yang K, Hu X. Synlett 2018; 29: 1617
- 21a McDonald LA, Abbanat DR, Barbieri LR, Bernan VS, Discafani CM, Greenstein M, Janota K, Korshalla JD, Lassota P, Tischler M, Carter GT. Tetrahedron Lett. 1999; 40: 2489
- 21b Wang T, Shirota O, Nakanishi K, Berova N, McDonald LA, Barbieri LR, Carter GT. Can. J. Chem. 2001; 79: 1786
- 22 Miyashita K, Sakai T, Imanishi T. Org. Lett. 2003; 5: 2683
- 23a Ando Y, Hanaki A, Sasaki R, Ohmori K, Suzuki K. Angew. Chem. Int. Ed. 2017; 56: 11460
- 23b Ando Y, Matsumoto T, Suzuki K. Synlett 2017; 28: 1040
- 23c Ando Y, Wakita F, Ohmori K, Suzuki K. Bioorg. Med. Chem. Lett. 2018; 28: 2663
- 23d Wakita F, Ando Y, Ohmori K, Suzuki K. Org. Lett. 2018; 20: 3928
- 23e Ando Y, Suzuki K. Chem. Eur. J. 2018; 24: 15955
- 23f Ando Y, Tanaka D, Sasaki R, Ohmori K, Suzuki K. Angew. Chem. Int. Ed. 2019; 58: 12507
- 24 Shu X, Chen C, Yu T, Yang J, Hu X. Angew. Chem. Int. Ed. 2021; 60: 18514
- 25a Corey EJ, Xu F, Noe MC. J. Am. Chem. Soc. 1997; 119: 12414
- 25b Corey EJ, Noe MC, Xu F. Tetrahedron Lett. 1998; 39: 5347
- 25c Corey EJ, Bo Y, Busch-Peterson J. J. Am. Chem. Soc. 1998; 120: 13000
- 26a Lygo B, Wainwright PG. Tetrahedron Lett. 1997; 38: 8595
- 26b Lygo B, Crosby J, Peterson JA. Tetrahedron Lett. 1999; 40: 1385
- 26c Lygo B. Tetrahedron Lett. 1999; 40: 1389
- 26d Lygo B, Crosby J, Peterson JA. Tetrahedron Lett. 1999; 40: 8671
- 27a Syper L. Tetrahedron Lett. 1967; 8: 4193
- 27b Snyder CD, Rapoport H. J. Am. Chem. Soc. 1972; 94: 227
For selected reviews on the biomimetic synthesis of natural products, please see:
For selected reviews on natural product synthesis through biomimetic dimerization, please see:
For selected reviews on biomimetic Diels–Alder reaction in natural product synthesis, please see: