Indole Diterpenoid Natural Products As the Inspiration for New Synthetic Methods and Strategies

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2017 Oct 4

PMID 28970940

Citations 19

Authors

Michael A Corsello

Junyong Kim

Neil K Garg

Affiliations

Soon will be listed here.

Abstract

Indole terpenoids comprise a large class of natural products with diverse structural topologies and a broad range of biological activities. Accordingly, indole terpenoids have and continue to serve as attractive targets for chemical synthesis. Many synthetic efforts over the past few years have focused on a subclass of this family, the indole diterpenoids. This minireview showcases the role indole diterpenoids have played in inspiring the recent development of clever synthetic strategies, and new chemical reactions.

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References

Teranishi T, Murokawa T, Enomoto M, Kuwahara S . Synthesis of (±)-terpendole E. Biosci Biotechnol Biochem. 2014; 79(1):11-5. DOI: 10.1080/09168451.2014.955455. View

Smith 3rd A, Kanoh N, Ishiyama H, Minakawa N, Rainier J, Hartz R . Tremorgenic indole alkaloids. The total synthesis of (-)-penitrem D. J Am Chem Soc. 2003; 125(27):8228-37. DOI: 10.1021/ja034842k. View

Rosen B, Werner E, OBrien A, Baran P . Total synthesis of dixiamycin B by electrochemical oxidation. J Am Chem Soc. 2014; 136(15):5571-4. PMC: 4004216. DOI: 10.1021/ja5013323. View

Tadross P, Stoltz B . A comprehensive history of arynes in natural product total synthesis. Chem Rev. 2012; 112(6):3550-77. DOI: 10.1021/cr200478h. View

Xu Z, Baunach M, Ding L, Hertweck C . Bacterial synthesis of diverse indole terpene alkaloids by an unparalleled cyclization sequence. Angew Chem Int Ed Engl. 2012; 51(41):10293-7. DOI: 10.1002/anie.201204087. View

Corsello M, Kim J, Garg N . Total synthesis of (-)-tubingensin B enabled by the strategic use of an aryne cyclization. Nat Chem. 2017; 9(10):944-949. PMC: 6994261. DOI: 10.1038/nchem.2801. View

Obradors C, Martinez R, Shenvi R . Ph(i-PrO)SiH2: An Exceptional Reductant for Metal-Catalyzed Hydrogen Atom Transfers. J Am Chem Soc. 2016; 138(14):4962-71. PMC: 4858193. DOI: 10.1021/jacs.6b02032. View

Hughes C, Miller A, Trauner D . An electrochemical approach to the guanacastepenes. Org Lett. 2005; 7(16):3425-8. DOI: 10.1021/ol047387l. View

Enomoto M, Morita A, Kuwahara S . Total synthesis of the tremorgenic indole diterpene paspalinine. Angew Chem Int Ed Engl. 2012; 51(51):12833-6. DOI: 10.1002/anie.201206299. View

10.

Sallam A, Houssen W, Gissendanner C, Orabi K, Foudah A, El Sayed K . Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors. Medchemcomm. 2013; 4(10). PMC: 3835464. DOI: 10.1039/C3MD00198A. View

11.

Jordan M, Wilson L . Microtubules as a target for anticancer drugs. Nat Rev Cancer. 2004; 4(4):253-65. DOI: 10.1038/nrc1317. View

12.

Xiong X, Zhang D, Li J, Sun Y, Zhou S, Yang M . Synthesis of indole terpenoid mimics through a functionality-tolerated Eu(fod)3 -catalyzed conjugate addition. Chem Asian J. 2015; 10(4):869-72. DOI: 10.1002/asia.201403312. View

13.

Neufeldt S, Sanford M . O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization. Org Lett. 2010; 12(3):532-5. PMC: 2830615. DOI: 10.1021/ol902720d. View

14.

George D, Kuenstner E, Pronin S . A Concise Approach to Paxilline Indole Diterpenes. J Am Chem Soc. 2015; 137(49):15410-3. PMC: 7556741. DOI: 10.1021/jacs.5b11129. View

15.

Ishida N, Sawano S, Masuda Y, Murakami M . Rhodium-catalyzed ring opening of benzocyclobutenols with site-selectivity complementary to thermal ring opening. J Am Chem Soc. 2012; 134(42):17502-4. DOI: 10.1021/ja309013a. View

16.

Ishikura M, Abe T, Choshi T, Hibino S . Simple indole alkaloids and those with a non-rearranged monoterpenoid unit. Nat Prod Rep. 2013; 30(5):694-752. DOI: 10.1039/c3np20118j. View

17.

Marcos I, Moro R, Costales I, Basabe P, Diez D . Sesquiterpenyl indoles. Nat Prod Rep. 2013; 30(12):1509-26. DOI: 10.1039/c3np70067d. View

18.

Nishimoto Y, Moritoh R, Yasuda M, Baba A . Regio- and stereoselective generation of alkenylindium compounds from indium tribromide, alkynes, and ketene silyl acetals. Angew Chem Int Ed Engl. 2009; 48(25):4577-80. DOI: 10.1002/anie.200901417. View

19.

Sharpe R, Johnson J . Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline. J Org Chem. 2015; 80(19):9740-66. PMC: 4598058. DOI: 10.1021/acs.joc.5b01844. View

20.

Acklin W, Fehr T, Stadler P . [The rôle of paliclavine in the biosynthesis of ergot alkaloids (author's transl)]. Helv Chim Acta. 1975; 58(8):2492-500. DOI: 10.1002/hlca.19750580829. View