Model studies toward a synthesis of asperaculin A: Exploration of iterative intramolecular Pauson-Khand reaction based strategies to access the dioxa[5.5.5.6]fenestrane framework

Tetrahedron Letters

Volumn 53, Issue 34, 2012, Pages 4558-4561

  Mehta, Goverdhan ^a   Khan, Tabrez Babu ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Dioxafenestrane; Intramolecular Pauson Khand reaction; Natural product synthesis; Tandem reactions

Indexed keywords

ASPERACULIN A; DITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PAUSON KHAND REACTION;

EID: 84864029875     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.06.059     Document Type: Article

References (18)

1. R.E. Corbett, D.R. Lauren, and R.T. Weavers J. Chem. Soc., Perkin Trans. 1 1979 1774 1790
2. R.E. Corbett, C.M. Couldwell, D.R. Lauren, and R.T. Weavers J. Chem. Soc., Perkin Trans. 1 1979 1791 1794
3. S.H. Shim, D.C. Swenson, J.B. Gloer, P.F. Dowd, and D.T. Wicklow Org. Lett. 8 2006 1225 1228
4. S.H. Shim, J.B. Gloer, and D.T. Wicklow J. Nat. Prod. 69 2006 1601 1605
5. For a recent review on fenestranes, see: R. Keese Chem. Rev. 106 2006 4787 4808
6. T. Gaich, and J. Mulzer J. Am. Chem. Soc. 131 2009 452 453
7. T. Gaich, and J. Mulzer Org. Lett. 12 2010 272 275
8. For a model study towards penifulvin A, see: T.K. Chakraborty, A.K. Chattopadhyay, R. Samanta, and R.S. Ampapathi Tetrahedron Lett. 51 2010 4425 4428
9. N. Ingavat, C. Mahidol, S. Ruchirawat, and P. Kittakoop J. Nat. Prod. 74 2011 1650 1652
10. G. Mehta, and K.S. Rao J. Org. Chem. 53 1988 425 427
11. For pioneering effort see: P.A. Wender, R. Teransky, M. deLong, S. Singh, A. Olivero, and K. Rice Pure. Appl. Chem. 62 1990 1597 1602
12. For a recent example, see: C.S. Penkett, J.A. Woolford, I.J. Day, and M.P. Coles J. Am. Chem. Soc. 132 2010 4 5
13. Selected examples: V.A. Smit, S.M. Buhanjuk, S.O. Simonyan, A.S. Shashkov, Y.T. Struchkov, A.I. Yanovsky, R. Caple, A.S. Gybin, L.G. Andersen, and A.J. Whiteford Tetrahedron Lett. 32 1991 2105 2108
14. D.H. Kim, S.U. Son, Y.K. Chung, and S.-G. Lee Chem. Commun. 2002 56 57
15. S.U. Son, K.H. Park, and Y.K. Chung J. Am. Chem. Soc. 124 2002 6838 6839
16. For an example of application of IPKR for fenestrane construction, see: M. Thommen, A.L. Veretenov, R. Guidetti-Grept, and R. Keese Helv. Chim. Acta 79 1996 461 475
17. For recent examples of IPKR from our group, see: G. Mehta, R. Samineni, and P. Srihari Tetrahedron Lett. 52 2011 1663 1666
18. G. Mehta, R. Samineni, and P. Srihari Tetrahedron Lett. 53 2012 829 832