Stereoselective total synthesis of (+)-sapinofuranone B

Tetrahedron

Volumn 67, Issue 25, 2011, Pages 4620-4627

  Yadav, J S ^a,b   Mandal, S S ^a   Reddy, J S S ^a   Srihari, P ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORANE DERIVATIVE; FURANONE DERIVATIVE; GAMMA METHOXYMETHOXYALLYL]DIISOPINOCAMPHEYLBORANE; SAPINOFURANONE B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RING OPENING METATHESIS POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79957778533     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.072     Document Type: Article

References (39)

1. R. Ling, M. Yoshida, and P.S. Mariano J. Org. Chem. 61 1996 4439 4449
2. H. Kiyota, Q.-W. Shi, and T. Oritani Nat. Prod. Lett. 16 2007 21 24
3. K.W. Cho, H.-S. Lee, J.-R. Rho, T.-S. Kim, S.J. Mo, and J. Shin J. Nat. Prod. 64 2001 664 667
4. S.P. Gunasekera, R.A. Isbrucker, R.E. Longley, A.E. Wright, S.A. Pomponi, and J.K. Reed J. Nat. Prod. 67 2004 110 111
5. For structure elucidation and first total synthesis, see S. Clough, M.E. Raggatt, T.J. Simpson, C.L. Willis, A. Whiting, and S.K. Wrigley J. Chem. Soc., Perkin Trans. 1 2000 2475 2481
6. A. Evidente, L. Sparapano, O. Fierro, G. Bruno, and A. Motta J. Nat. Prod. 62 1999 253 256
7. For other total synthesis see:
8. P. Kumar, V.S. Naidu, and P. Gupta J. Org. Chem. 70 2005 2843 2846
9. N. Kutsumura, T. Yokoyama, T. Ohgiya, and S. Nishiyama Tetrahedron Lett. 47 2006 4133 4136
10. For our contributions on lactone containing molecules see
11. P. Srihari, E. Vijaya Bhasker, A. Bal Reddy, and J.S. Yadav Tetrahedron Lett. 50 2009 2420 2424
12. P. Srihari, K. Ravindar, R. Somaiah, and J.S. Yadav Synth. Commun. 2008 1389 1397
13. P. Srihari, B.P. Kumar, and P. Subbarayudu Tetrahedron Lett. 48 2007 6977-6981
14. P. Srihari, E.V. Bhasker, S.J. Harshavardhan, and J.S. Yadav Synthesis 2006 4041 4045
15. J.S. Yadav, I. Prathap, and T.B. Padmaja Tetrahedron Lett. 47 2006 3773 3776
16. J.S. Yadav, K. Vishweshwar Rao, M. Sridhar Reddy, and A.R. Prasad Tetrahedron Lett. 47 2006 4393 4395
17. J.S. Yadav, J.S.S. Reddy, S.S. Mandal, and P. Srihari Synlett 2010 2636 2638
18. D. Seebach R. Scheffold, Hungerbuhler Modern Synthetic Methods Vol. 2 1980 Salle and Sauerlander Frankfurt and Aarau 91 171
19. H. Iida, N. Yamazaki, and C. Kibayashi J. Org. Chem. 52 1987 3337 3342
20. Similar procedure was adopted as given in J. Mulzer, M. Kappert, G. Huttner, and I. Jibril Angew. Chem., Int. Ed. Engl. 23 1984 704 705 The de was determined by Reverse Phase HPLC column: water HRC18 300×3.9 mm, 6 μ. Mobile Phase used was 75% acetonitrile+25% Water. Flow Rate: 1.0 mL/min
21. A. Furstner, M.D.B. Fenster, B. Fasching, C. Godbout, and K. Radkowski Angew. Chem. 118 2006 5632 5636
22. J.S. Yadav, M.C. Chander, and B.V. Joshi Tetrahedron Lett. 29 1988 2737 2740
23. J.S. Yadav, K.D. Prasad, and G.V.M. Sharma Tetrahedron 46 1990 7033 7046
24. J.S. Yadav, and M.C. Chander Tetrahedron Lett. 31 1990 4349 4350
25. O. Mitsunobu Synthesis 1981 1 28
26. A.B. Charette, and B. Cote J. Am. Chem. Soc. 117 1995 12721 12732
27. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467 4470
28. Q. Yu, Y. Wu, H. Ding, and Y.-L. Wu J. Chem. Soc., Perkin Trans. 1 1999 1183 1188
29. D. Madec, and J.-P. Férézou Tetrahedron Lett. 38 1997 6661 6664
30. I. Izzo, S. Decaro, F. De Riccardis, and A. Spinella Tetrahedron Lett. 41 2000 3975 3978
31. W. Boland, N. Schroer, and C. Sieler Helv. Chim. Acta 70 1987 1025 1040
32. B.W. Gung, J.P. Melnick, M.A. Wolf, J.A. Marshall, and S. Beaudoin J. Org. Chem. 59 1994 5609 5613
33. G.D. Joly, and E.N. Jacobsen Org. Lett. 4 2002 1795 1798
34. H.C. Brown, P.K. Jadhav, and K.S. Bhat J. Am. Chem. Soc. 110 1988 1535 1538 The de was determined to be >99% by Reverse Phase HPLC column: Water HRC18, 300×3.9 mm, 6 μ. Mobile Phase used was 30% Acetonitrile+70% Water. Flow Rate: 1.0 mL/min. The ee was analyzed on chiral column using chiral pack IA, 250×4.6 mm, 5 μm, UV254 nm, Hexane/2-propanol (85:15) as mobile phase, flow rate-1.0 mL/min
35. M.T. Crimmins, and M.W. Haley Org. Lett. 8 2006 4223 4225
36. T. Satoh, K. Nanba, and S. Suzuki Chem. Pharm. Bull. 19 1971 817 820
37. S. Ohira Synth. Commun. 19 1989 561 564
38. S. Muller, B. Liepold, G.J. Roth, and H.J. Bestmann Synlett 1996 521 522
39. G.J. Roth, B. Liepold, S.J. Muller, and H.J. Bestmann Synthesis 2004 59 62