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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 14
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Synthetic Communications Review

Stereoselective total synthesis of paecilomycin E and F and its two congeners Cochliomycin C and 6-epi-Cochliomycin C

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Pages 1867-1875 | Received 30 Jan 2018, Published online: 18 Jun 2018

References

  • Delmotte, P.; Delmotte, P. A New Antifungal Substance of Fungal Origin. J. Nature 1953, 171, 344–345. DOI:10.1038/171344a0.
  • Stob, M.; Baldwin, R. S.; Tuite, J.; Andrews, F. N.; Gillette, K. G. Isolation of an Anabolic, Uterotrophic Compound from Corn Infected with Gibberella Zeae. Nature 1962, 196, 1318–1319. DOI:10.1038/1961318a0.
  • Ellstad, G. A.; Lovell, F. M.; Perkinson, N. A.; Hargreaves, R. T.; McGahren, W. J. Formation of 14.alpha.-Cardenolides from 21-Acetoxy-20-Keto Steroids. J. Org. Chem. 1978, 43, 2334–2343. DOI:10.1021/jo00406a007.
  • Nair, M. S. R.; Carey, S. T. Metabolites of Pyrenomycetes XIII: Structure of (+) Hypothemycin, an Antibiotic Macrolide from Hypomyces Trichothecoides. Tetrahedron Lett. 1980, 21, 2011–2012. DOI:10.1016/S0040-4039(00)71472-9.
  • Abid, E. S.; Ounes, Z.; Hassen, W.; Baudrimont, I.; Creppy, E.; Bacha, H. Cytotoxicity, Inhibition of DNA and Protein Syntheses and Oxidative Damage in Cultured Cells Exposed to Zearalenone. Toxicol. In Vitro 2004, 18, I–474. DOI:10.1016/j.tiv.2003.12.011.
  • Furstner, A.; Langemann, K. Total Syntheses of (+)-Ricinelaidic Acid Lactone and of (−)-Gloeosporone Based on Transition-Metal-Catalyzed C − C Bond Formations. J. Am. Chem. Soc. 1997, 119, 9130–9166. DOI:10.1021/ja9719945.
  • Kwon, H. J.; Yoshida, M.; Abe, K.; Horinouchi, S.; Beppu, T. Radicicol, an Agent Inducing the Reversal of Transformed Phenotypes of src-Transformed Fibroblasts. Biosci. Biotechnol. Biochem. 1992, 56, 538–539. DOI:10.1271/bbb.56.538.
  • Roe, S. M.; Prodromou, C.; O’brien, R.; Ladbury, J. E.; Piper, P. W.; Pearl, L. H. Structural Basis for Inhibition of the Hsp90 Molecular Chaperone by the Antitumor Antibiotics Radicicol and Geldanamycin. J. Med. Chem. 1999, 42, 260–266. DOI:10.1021/jm980403y.
  • Couladouros, E. A.; Mihou, A. P.; Bouzas, E. A. First Total Synthesis of Trans- and Cis-Resorcylide: remarkable Hydrogen-Bond-Controlled, Stereospecific Ring-Closing Metathesis. Org. Lett. 2004, 6, 977–980. DOI:10.1021/ol0400037.
  • Lampilas, M.; Lett, R. Convergent Stereospecific Total Synthesis of Monochiral Monocillin I Related Macrolides. Tetrahedron Lett. 1992, 33, 773–776. DOI:10.1016/S0040-4039(00)77712-4.
  • Lampilas, M.; Lett, R. Convergent Stereospecific Total Synthesis of Monocillin I and Monorden (or Radicicol). Tetrahedron Lett. 1992, 33, 777–780. DOI:10.1016/S0040-4039(00)77713-6.
  • For contributions on synthesis of resorcylic acid lactones, see: Napolitano, C.; Murphy, P. V. Resorcylic Acid Lactones. In Natural Lactones and Lactams: Synthesis Occurrence and Bio-Logical Activity, Janecki T., Ed.; Wiley-VCH: Weinheim, Germany, 2014; pp 273–319, chapter 7.
  • Ayer, W. A.; Lee, S. P.; Tsuneda, A.; Hiratsuka, Y. The Isolation, Identification, and Bioassay of the Antifungal Metabolites Produced by Monocillium Nordinii. Can. J. Microbiol. 1980, 26, 766–773. DOI:10.1139/m80-133.
  • Nair, M. S. R.; Carey, S. T. Metabolites of Pyrenomycetes XIII: Structure of (+) Hypothemycin, an Antibiotic Macrolide from Hypomyces Trichothecoides. Tetrahedron Lett. 1980, 21, 2011–2012. DOI:10.1016/S0040-4039(00)71472-9.
  • Mirrington, R. N.; Ritchie, E.; Shoppee, C. W.; Taylor, W. C.; Sternhell, S. Tetrahedron Lett. 1964, 5, 365–370. DOI:10.1016/0040-4039(64)80029-0.
  • Hellwig, V.; Mayer-Bartschmid, A.; Müller, H.; Greif, G.; Kleymann, G.; Zitzmann, W.; Tichy, H.-V.; Stadler, M. Pochonins a-F, New Antiviral and Antiparasitic Resorcylic Acid Lactones from Pochonia Chlamydosporia Var. catenulata. J. Nat. Prod. 2003, 66, 829–837. DOI:10.1021/np020556v.
  • Shao, C. L.; Wu, H. X.; Wang, C. Y.; Liu, Q. A.; Xu, Y.; Wei, M. Y.; Qian, P. Y.; Gu, Y. C.; Zheng, C. J.; She, Z. G.; Lin, Y. C. Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus Lunatus. J. Nat. Prod. 2011, 74, 629–633. DOI:10.1021/np100641b.
  • Zhang, W.; Shao, C.; Chen, M.; Liu, Q. A.; Wang, C. Y. Brominated Resorcylic Acid Lactones from the Marine-Derived Fungus Cochliobolus Lunatus Induced by Histone Deacetylase Inhibitors. Tetrahedron Lett. 2014, 55, 4888–4891. DOI:10.1016/j.tetlet.2014.06.096.
  • Xu, L.; He, Z.; Xue, J.; Chen, X.; Wei, X. Beta-Resorcylic Acid Lactones from a Paecilomyces Fungus. J. Nat. Prod. 2010, 73, 885–889. DOI:10.1021/np900853n.
  • Xu, L.; He, Z.; Xue, J.; Chen, X.; Wei, X. Correction to β-Resorcylic Acid Lactones from a Paecilomyces Fungus. J. Nat. Prod. 2012, 75, 1006–1006. DOI:10.1021/np300293b.
  • Shao, C. L.; Wu, H. X.; Wang, Ch, Y.; Liu, Q.; A.; Xu, Y.; Wei, M. Y.; Qian, P. Y.; Gu, Y. C.; Zheng, C. J.; She, Z. G.; Lin, Y. C. Correction to Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus Lunatus. J. Nat. Prod. 2013, 76, 302–302. DOI:10.1021/np400079t.
  • Srihari, P.; Mahankali, B.; Rajendraprasad, K. Stereoselective Total Synthesis of Paecilomycin E. Tetrahedron Lett. 2012, 53, 56–58. DOI:10.1016/j.tetlet.2011.10.137
  • Pal, P.; Jana, N.; Nanda, S. Asymmetric Total Synthesis of Paecilomycin E, 10′-Epi-Paecilomycin E and 6′-Epi-Cochliomycin C. Org. Biomol. Chem. 2014, 12, 8257–8274. DOI:10.1039/C4OB01400F.
  • Mohapatra, D. K.; Reddy, D. S.; ArjunReddy, N. M.; Yadav, J. S. Stereoselective Total Syntheses of Paecilomycins E and F through a Protecting Group Directed Diastereoselective Intermolecular Nozaki-Hiyama-Kishi (NHK) Reaction. Eur. J. Org. Chem. 2014, 2014, 5023–5032. DOI:10.1002/ejoc.201402133.
  • Mahankali, B.; Srihari, P. A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′- Epi-Cochliomycin C. Eur. J. Org. Chem. 2015, 2015, 3983–3993. DOI:10.1002/ejoc.201500395.
  • Bhunia, N.; Das, B. Stereoselective Total Synthesis of Paecilomycins E and F. Synthesis 2015, 47, 1499–1509. DOI:10.1055/s-0034-1380400.
  • Sabitha, G.; Sudhakar, K.; Srinivas, C.; Yadav, J. Stereoselective Synthesis of a Mevinic Acid Analogue. S. Synthesis 2007, 2007, 705–708. DOI:10.1055/s-2007-965904.
  • Mohapatra, D. K.; Das, P. P.; Reddy, D. S.; Yadav, J. S. First Total Syntheses and Absolute Configuration of Rugulactone and 6(R)-(4′-oxopent-2′-enyl)-5,6-dihydro-2H-pyran-2-one. Tetrahedron Lett. 2009, 50, 5941–5944. DOI:10.1016/j.tetlet.2009.08.028.
  • Mohapatra, D. K.; Reddy, D. S.; Ramaiah, M. J.; Ghosh, S.; Pothula, V.; Lunavath, S.; Thomas, S.; Valli. S. N.; Bhadra, M. P.; Yadav, J. S. Rugulactone Derivatives Act as Inhibitors of NF-κB Activation and Modulates the Transcription of NF-κB Dependent Genes in MDA-MB-231cells. Bioorg. Med. Chem. Lett. 2014, 24, 1389–1396. DOI:10.1016/j.bmcl.2014.01.030.
  • Mohapatra, D. K.; Reddy, D. S.; Reddy, G. S.; Yadav, J. S. Synthesis of the C-8-C-24 Fragment of Maltepolide C by Using a Tandem DiHydroxylation/S N 2 Cyclization Sequence. Eur. J. Org. Chem. 2015, 2015, 5266–5274. DOI:10.1002/ejoc.201500629.
  • Reddy, D. S.; Mukhina, O. A.; Cronk, W. C.; Kutateladze, A. G. Polyheterocycle-carbohydrate Chimeras: Photoassisted Synthesis of 2,5-epoxybenzoxacines and 2,5-epoxybenzazocine Scaffolds and Their Postphotochemical Hydroxylations. Pure Appl. Chem. 2017, 89, 259–268. DOI:10.1515/pac-2016-0915.
  • Reddy, D. S.; Kutateladze, A. G. Structure Revision of an Acorane Sesquiterpene Cordycepol a. Org. Lett. 2016, 18, 4860–4863. DOI:10.1021/acs.orglett.6b02341.
  • Reddy, D. S.; Kutateladze, A. G. Computational Structure Revision of a Longipinane Derivative Meridane. Tetrahedron Lett. 2016, 57, 4727–4729. DOI:10.1016/j.tetlet.2016.09.030.
  • Kutateladze, A. G.; Reddy, D. S. High-Throughput in Silico Structure Validation and Revision of Halogenated Natural Products Is Enabled by Parametric Corrections to DFT-Computed 13C NMR Chemical Shifts and Spin-Spin Coupling Constants. J. Org. Chem. 2017, 82, 3368–3381. DOI:10.1021/acs.joc.7b00188.
  • Krishanu, S.; Pradeep, K. Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-epi-Stagonolide CEmploying Chiral Hexane-1,2,3,5-tetraol Derivatives as BuildingBlocks. Eur. J. Org. Chem. 2016, 4696–4710. DOI:10.1016/j.tetlet.2009.08.028.
  • Mohapatra, D. K.; Reddy, D. S.; Mallampudi, N. A.; Gaddam, J.; Polepalli, S.; Jain, N.; Yadav, J. S. The Protecting-Group Directed Diastereoselective Nozaki-Hiyama-Kishi (NHK) Reaction: total Synthesis and Biological Evaluation of Zeaenol, 7-Epi-Zeaenol and Its Analogues. Org. Biomol. Chem. 2014, 12, 9683–9695. DOI:10.1039/C4OB01811G.
  • Chattopadhyay, A. (R)-2,3-O-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Homoallyl and Homopropargyl Alcohols in Aqueous Medium. J. Org. Chem. 1996, 61, 6104–6107. DOI:10.1021/jo9604696.
  • Bhattacharjee, A.; Sequil, O. R.; De Brabander, J. K. Synthesis of Side Chain Truncated Apicularen a. Tetrahedron Lett. 2000, 41, 8069–8073. DOI:10.1016/S0040-4039(00)01403-9.

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