An enantiodivergent formal synthesis of paecilomycine A

Tetrahedron Letters

Volumn 53, Issue 7, 2012, Pages 829-832

  Mehta, Goverdhan ^a   Samineni, Ramesh ^a,b   Srihari, Pabbaraja ^b  

^a UNIVERSITY OF HYDERABAD   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,4 Chirality transfer protocol; Intramolecular Pauson Khand reaction; Stereoselective Luche reduction; TBS migration

Indexed keywords

PAECILOMYCINE A; TRICHOTHECENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; PAUSON KHAND REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84855828564     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.015     Document Type: Article

References (34)

1. J.F. Grove Nat. Prod. Rep. 5 1988 187 209
2. J.F. Grove Nat. Prod. Rep. 10 1993 429 448
3. B.B. Jarvis, G.P. Stahly, G. Pavanasasivam, J.O. Midiwo, T. DeSilva, C.E. Holmlund, E.P. Mazolla, and R.F. Geoghegan Jr. J. Org. Chem. 47 1982 1117 1124
4. B.B. Jarvis, V.M. Vrudhula, J.O. Midiwo, and E.P. Mazzola J. Org. Chem. 48 1983 2576 2578
5. D.G. Corley, G.E. Rottinghaus, and M.S. Tempesta Tetrahedron Lett. 27 1986 427 430
6. P. Mohr, C. Tamm, W. Zucher, and M. Zehnder Helv. Chim. Acta 67 1984 406 412
7. J. Gutzwiller, R. Mauli, H.P. Sigg, and C. Tamm Helv. Chim. Acta 47 1964 2234 2262
8. D.G. Corley, G.E. Rottinghaus, and M.S. Tempesta J. Org. Chem. 52 1987 4405 4408
9. D.M. Fort, C.L. Barnes, and M.S. Tempesta J. Nat. Prod. 56 1993 1890 1897
10. H. Kikuchi, Y. Miyagawa, Y. Sahashi, S. Inatomi, A. Haganuma, N. Nakahata, and Y. Oshima J. Org. Chem. 69 2004 352 356
11. H. Kikuchi, Y. Miyagawa, Y. Sahashi, S. Inatomi, A. Haganuma, N. Nakahata, and Y. Oshima Tetrahedron Lett. 45 2004 6225 6228
12. T. Kita, Y. Takaya, Y. Oshima, T. Ohta, K. Aizawa, T. Hirano, and T. Inakuma Tetrahedron 54 1998 11877 11886
13. Y. Obara, H. Kobayashi, T. Ohta, Y. Ohizumi, and N. Nakahata Mol. Pharmacol. 59 2001 1287 1297
14. S.-J. Min, and S.-J. Danishefsky Angew. Chem., Int. Ed. 46 2007 2199 2202
15. For related work from our group, see: G. Mehta, and R. Singh Tetrahedron Lett. 46 2005 2079 2082
16. G. Mehta, and R. Singh Angew. Chem., Int. Ed. 45 2006 953 955
17. G. Mehta, and H.M. Shinde Tetrahedron Lett. 48 2007 8297 8300
18. G. Mehta, and P. Maity Tetrahedron Lett. 48 2007 8865 8868
19. G. Mehta, and B.A. Bhat Tetrahedron Lett. 50 2009 2474 2477
20. G. Mehta, and P. Maity Tetrahedron Lett. 52 2011 1749 1752
21. G. Mehta, and P. Maity Tetrahedron Lett. 52 2011 1753 1756
22. G. Mehta, and P. Maity Tetrahedron Lett. 52 2011 5161 5165
23. G. Mehta, R. Samineni, and P. Srihari Tetrahedron Lett. 52 2011 1663 1666
24. For some reviews on Pauson-Khand reactions see: K.M. Brummnod, and J.L. Kent Tetrahedron 56 2000 3263 3283
25. S.E. Gibson, and A. Stevenazzi Angew. Chem., Int. Ed. 42 2003 1800 1810
26. Preparation of (9): R. Adams, C.M. Smith, and S. Loewe J. Am. Chem. Soc. 1942 2087 2089
27. C. Djerassi, and G.W. Krakower J. Am. Chem. Soc. 1958 237 242
28. J.L. Luche J. Am. Chem. Soc. 100 1978 2226 2227
29. Y. Ito, T. Hirao, and T. Saegusa J. Org. Chem. 43 1978 1011
30. Chiral HPLC: Column: chiral pak IC 250X4.6 mm, 5microns, mobile phase: 3% IPA-HEXANE, flow rate: 1.0 ml/min.
31. S. Ohira Synth. Commun. 19 1989 561 564
32. S. Muller, B. Liepold, G.J. Roth, and H.J. Bestmann Synlett 1996 521 552
33. D. Seyferth, R.S. Marmor, and P. Hibert J. Org. Chem. 36 1971 1379 1386
34. J.C. Gilbert, and U. Weerasooriya J. Org. Chem. 44 1979 4997 4998