An intramolecular [4+3]-cycloaddition approach to rameswaralide inspired by biosynthesis speculation

Tetrahedron Letters

Volumn 50, Issue 52, 2009, Pages 7310-7313

  Pattenden, Gerald ^a   Winne, Johan M ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BUTENOLIDE; DITERPENE; FURAN; POLYCYCLIC HYDROCARBON; RAMESWARALIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CHROMATOGRAPHY; CYCLOADDITION;

EID: 70449106131     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.046     Document Type: Article

References (22)

1. Ramesh P., Reddy N.S., Venkateswarlu Y., Reddy M.V.R., and Faulkner D.J. Tetrahedron Lett. 39 (1998) 8217-8220
2. Venkateswarlu Y., Biabani M.A.F., Reddy M.V.R., Rao T.P., Kunwar A.C., and Faulkner D.J. Tetrahedron Lett. 35 (1994) 2249-2252
3. Anjaneyulu A.S.R., Sagar K.S., and Venugopal M.J.R.V. Tetrahedron 51 (1995) 10997-11010
4. A seco-diterpene, havellockate, analogous to structures 2 and 3 has also been isolated from Sinularia granosa:. Anjaneyulu A.S.R., Venugopal M.J.R.V., Sarada P., Clardy J., and Lobkovsky E. Tetrahedron Lett. 39 (1998) 139-142
5. Stonik V.A., Kapustina I.I., Kalinovsky A.I., Dmitrenok P.S., and Grebnev B.B. Tetrahedron Lett. 43 (2002) 315-317
6. Pattenden, G. The Robert Robinson Award Lecture of The Royal Society of Chemistry, University of Southampton, England, April 2007, and Gordon Research Conference: Heterocyclic Compounds, Rhode Island, USA, June 2007.
7. Roethle P.A., and Trauner D. Nat. Prod. Rep. 25 (2008) 298-317
8. The stereochemistries of rameswaralide 1 and plumarellide 4 were determined by analysis of coupling constants and NOE(SY) correlations in their 1H NMR spectra; see Refs. 1,5. They were shown to be epimeric at the t -hydroxy centre (C-8) in their cyclopentane rings. Similarly, plumarellic acid ethyl ester 5 is epimeric with the mandapamates 2 and 3, at the same carbon centre.
9. The suggestion of a relationship between the carbon skeletons in rameswaralide 1 and isomandapamate 3 was first made by Venkateswarlu and Faulkner; see Ref. 1.
10. A limited number of naturally occurring enol ether-cyclic ketal metabolites from furanobutenolide cembranes have been isolated:. Abramson S.N., Trischman J.A., Tapiolas D.M., Harold E.E., Fenical W., and Taylor P. J. Med. Chem. 34 (1991) 1798-1804
11. Venkateswarlu Y., Sridevi K.V., and Rama Rao M. J. Nat. Prod. 62 (1999) 756-758
12. Kamel H.N., Ferreira D., Garcia-Fernandez L.F., and Slattery M. J. Nat. Prod. 70 (2007) 1223-1227
13. Grote D., Dahse H.-M., and Seifert K. Chem. Biodivers. 5 (2008) 2449-2456
14. Saito S., Hasegawa T., Inaba N., Nishida R., Fujii T., Nomizu S., and Muriwake T. Chem. Lett. (1984) 1389-1392
15. Doroh B., and Sulikowski G.A. Org. Lett. 8 (2006) 903-906
16. The diastereoisomer 17 was used in this model study, so as to allow us to employ its t-OH epimer in contemporaneous studies towards rameswaralide itself. Compound 17 has the same stereochemistry at the t-OH centre in plumarellide 4 but is epimeric with the same centre in rameswaralide.
17. For an early example of this tandem Knoevenagel condensation-cyclisation of α-epoxy aldehydes to give furanmethanols, see:. Williams P.H., Payne G.B., Sullivan W.J., and Van Ess P.R. J. Am. Chem. Soc. 82 (1960) 4883-4888
18. Cf.:. Gupta Y.N., Doa M.J., and Houk K.N. J. Am. Chem. Soc. 104 (1982) 7336-7338
19. Moiseev A.M., Balenkova E.S., and Nenajdenko V.G. Russ. Chem. Bull., Int. Ed. 55 (2006) 141-146
20. See:. Wenkert E., Moeller P.D.R., and Piettre S.R. J. Am. Chem. Soc. 110 (1988) 7188-7194
21. For other synthetic approaches, see:. Srikrishna A., and Dethe D.H. Org. Lett. 6 (2004) 165-168
22. Mehta G., and Lakshminath S. Tetrahedron Lett. 47 (2006) 327-330