Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A

Journal of Natural Products

Volumn 78, Issue 8, 2015, Pages 1963-1968

  Lan, Ping ^a   White, Lauren E ^a   Taher, Ehab S ^a   Guest, Prudence E ^a   Banwell, Martin G ^a   Willis, Anthony C ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERGILLUSOL A; ASPERPENTYN; CARBON 13; NATURAL PRODUCT; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; CYCLOHEXENE DERIVATIVE; EPOXIDE; TYROSINE;

ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CHEMOENZYMATIC SYNTHESIS; CHROMATOGRAPHY; DIHYDROXYLATION; DRUG STRUCTURE; ENANTIOMER; NUCLEOPHILICITY; RING OPENING; SONOGASHIRA REACTION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS; ANALOGS AND DERIVATIVES; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

BIOLOGICAL PRODUCTS; CYCLOHEXENES; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM; TYROSINE;

EID: 84940541130     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00304     Document Type: Article

References (33)

1. Rukachaisirikul, V.; Rungsaiwattana, N.; Klaiklay, S.; Phongpaichit, S.; Borwornwiriyapan, K.; Sakayaroj, J. J. Nat. Prod. 2014, 77, 2375-2382 10.1021/np500324b
2. Rukachaisirikul, V.; Rungsaiwattana, N.; Klaiklay, S.; Pakawatchai, C.; Saithong, S.; Phongpaichit, S.; Borwornwiriyapan, K.; Sakayaroj, J. Tetrahedron 2013, 69, 11116-11121 10.1016/j.tet.2013.11.009
3. Liu, Z.; Jensen, P. R.; Fenical, W. Phytochemistry 2003, 64, 571-574 10.1016/S0031-9422(03)00272-3
4. Davis, R. A.; Andjic, V.; Kotiw, M.; Shivas, R. G. Phytochemistry 2005, 66, 2771-2775 10.1016/j.phytochem.2005.09.004
5. Mühlenfeld, A.; Achenbacht, H. Phytochemistry 1988, 27, 3853-3855 10.1016/0031-9422(88)83031-0
6. Klaiklay, S.; Rukachaisirikul, V.; Tadpetch, K.; Sukpondma, Y.; Phongpaichit, S.; Buatong, J.; Sakayaroj, J. Tetrahedron 2012, 68, 2299-2305 10.1016/j.tet.2012.01.041
7. Smetanina, O. F.; Yurchenko, A. N.; Kalinovskii, A. I.; Khudyakova, Y. V.; Kirichuk, N. N.; Pivkin, M. V.; Afiyatullov, S. S.; Mikhailov, V. V. Chem. Nat. Compd. 2014, 50, 1120-1121 10.1007/s10600-014-1178-3
8. Kaur, A.; Rogers, K. D.; Swenson, D. E.; Dowd, P. F.; Wicklow, D. T.; Gloer, J. B. Mycology 2014, 5, 120-129 10.1080/21501203.2014.931309
9. Pinkerton, D. M.; Banwell, M. G.; Willis, A. C. Org. Lett. 2009, 11, 4290-4293 10.1021/ol9016657
10. Pinkerton, D. M.; Banwell, M. G.; Willis, A. C. Aust. J. Chem. 2009, 62, 1639-1645 10.1071/CH09469
11. Pinkerton, D. M.; Banwell, M. G.; Willis, A. C. Acta Crystallogr., Sect. E: Struct. Rep. Online 2010, 66, o342-o343 10.1107/S1600536810000620
12. White, L. V.; Dietinger, C. E.; Pinkerton, D. M.; Willis, A. C.; Banwell, M. G. Eur. J. Org. Chem. 2010, 4365-4367 10.1002/ejoc.201000642
13. Ma, X.; Banwell, M. G.; Willis, A. C. J. Nat. Prod. 2013, 76, 1514-1518 10.1021/np4002866
14. Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichim. Acta 1999, 32, 35-62
15. Banwell, M. G.; Edwards, A. J.; Harfoot, G. J.; Jolliffe, K. A.; McLeod, M. D.; McRae, K. J.; Stewart, S. G.; Vögtle, M. Pure Appl. Chem. 2003, 75, 223-229 10.1351/pac200375020223
16. Johnson, R. A. Org. React. 2004, 63, 117-264 10.1002/0470020504.ch7
17. Hudlicky, T.; Reed, J. W. Synlett 2009, 2009, 685-703 10.1055/s-0028-1087946
18. Bon, D. J.-Y. D.; Lee, B.; Banwell, M. G.; Cade, I. A. Chim. Oggi 2012, 30 (No. 5, Chiral Technologies Supplement) 22-27
19. Li, J.; Park, S.; Miller, R. L.; Lee, D. Org. Lett. 2009, 11, 571-574 10.1021/ol802675j
20. Barros, M. T.; Maycock, C. D.; Ventura, M. R. Chem.-Eur. J. 2000, 6, 3991-3996 10.1002/1521-3765(20001103)6:21<3991::AID-CHEM3991>3.3.CO;2-M
21. Tachihara, T.; Kitahara, T. Tetrahedron 2003, 59, 1773-1780 10.1016/S0040-4020(03)00119-4
22. Mehta, G.; Roy, S.; Pan, S. C. Tetrahedron Lett. 2012, 53, 4093-4095 10.1016/j.tetlet.2012.05.115
23. Boyd, D. R.; Sharma, N. D.; Llamas, N. M.; Malone, J. F.; O'Dowd, C. R.; Allen, C. C. R. Org. Biomol. Chem. 2005, 3, 1953-1963 10.1039/b502009c
24. Mattocks, A. R. J. Chem. Soc. 1964, 4840-4845 10.1039/jr9640004840
25. Boyd, D. R.; Sharma, N. D.; Acaru, C. A.; Malone, J. F.; O'Dowd, C. R.; Allen, C. C. R.; Stevenson, P. J. Org. Lett. 2010, 12, 2206-2209 10.1021/ol100525r
26. Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data
27. Banwell, M. G.; Liu, L.; Parish, C. R.; Freeman, C. G. Linked Cyclitols and their Polysulfated Derivatives, International Patent No. WO03004454 A1, 2003.
28. Banwell, M. G.; Haddad, N.; Hudlicky, T.; Nugent, T. C.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1997, 1779-1791 10.1039/a700733g
29. Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier: Amsterdam, 2005; pp 424-425.
30. Saito, H.; Nishimura, Y.; Kondo, S.; Umezawa, H. Chem. Lett. 1987, 16, 799-802 10.1246/cl.1987.799
31. Schwartz, B. D.; White, L. V.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2011, 76, 8560-8563 and references therein. 10.1021/jo2016899
32. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925 10.1021/jo00408a041
33. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520 10.1021/om9503712