Stereoselective total synthesis of (+)-boronolide

Tetrahedron

Volumn 62, Issue 6, 2006, Pages 1193-1198

  Boruwa, Joshodeep ^a   Barua, Nabin C ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

Asymmetric dihydroxylation; Asymmetric Henry reaction; Boronolide; Chiral allylation; Nef reaction; Ring closing metathesis

Indexed keywords

BORONOLIDE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 29744452186     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.070     Document Type: Article

References (39)

1. A brief account of this work was presented by the authors in JNOST symposium held at National Chemical Laboratory, Pune (India) during November 2004.
2. N.C. Franca, and J. Polonsky C. R. Acad. Sci. (Paris) 273 1971 439
3. M.T. Davis-Coleman, and D.E. Rivett Phytochemistry 26 1987 3047 3050
4. L. Van Puyvelde, N. De Kimple, S. Dube, M. Chagnon-Dube, Y. Boily, F. Borremans, N. Schamp, and M.J.O. Anteunis Phytochemistry 20 1981 2753 2755
5. C.W. Jefford, and M.-C. Moullin Helv. Chim. Acta 74 1991 335 342
6. H. Nagano, and H. Yasui Chem. Lett. 1992 1045 1048
7. T. Honda, S. Horiuchi, H. Mizutani, and K. Kanai J. Org. Chem. 61 1996 4944 4948
8. A.K. Ghosh, and G. Bilcer Tetrahedron Lett. 41 2000 1003 1006
9. M. Chandrasekhar, S. Raina, and V.K. Singh Tetrahedron Lett. 41 2000 4969 4972
10. M. Carda, S. Rodriguez, B. Segovia, and J.A. Marco J. Org. Chem. 67 2002 6560 6563
11. J. Murga, E. Falomir, M. Carda, and J.A. Marco Tetrahedron: Asymmetry 13 2002 2317 2327
12. B.M. Trost, and V.S.C. Yeh Org. Lett. 4 2002 3513 3516
13. M. Chandrasekhar, K.L. Chandra, and V.K. Singh J. Org. Chem. 68 2003 4039 4045
14. S.G. Hu, T.S. Hu, and Y.L. Wu Org. Biomol. Chem. 2 2004 2305 2310
15. S.V. Naidu, P. Gupta, and P. Kumar Tetrahedron Lett. 46 2005 2129 2131
16. B.K. Sarma, and N.C. Barua Tetrahedron 49 1993 2253 2260
17. B.K. Sarma, and N.C. Barua Indian J. Chem., Sect B 32B 1993 615 617
18. A.K. Saikia, M.J. Hazarika, N.C. Barua, M.S. Bezbarua, R.P. Sharma, and A.C. Ghosh Synthesis 1996 981 985
19. M.S. Bezbarua, A.K. Saikia, N.C. Barua, and D. Kalita Synthesis 1996 1289 1290
20. D. Kalita, A.T. Khan, N.C. Barua, and G. Bez Tetrahedron 55 1999 5177 5181
21. G. Bez, M.S. Bezbarua, A.K. Saikia, and N.C. Barua Synthesis 2000 537 540
22. B. Kalita, N.C. Barua, M.S. Bezbarua, and G. Bez Synlett 2001 1411 1414
23. J.C. Borah, S. Gogoi, J. Boruwa, B. Kalita, and N.C. Barua Tetrahedron Lett. 45 2004 3689 3691
24. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483 2547
25. H. Becker, and K.B. Sharpless Angew. Chem., Int. Ed. 35 1996 448 451
26. The enantiomeric excess was measured by HPLC analysis carried out in a Waters 510 HPLC system. Chiracel OD packed in a SS column of 4.6 mm i.d×250 m was used. Isocratic elution was applied with a mobile phase consisting of n-hexane 90% and isopropanol 10% at a flow rate of 0.8 mL/min and a pressure 125 psi, UV detector at 243 nm.
27. P. Phukan Tetrahedron Lett. 45 2004 4785 4787
28. H. Sasai, T. Suzuki, T. Arai, and M. Shibasaki J. Am. Chem. Soc. 114 1992 4418 4420
29. H. Sasai, T. Suzuki, N. Itoh, and M. Shibasaki Tetrahedron Lett. 34 1993 851 854
30. Isolated yield of the major diastereomer.
31. Diastereomeric ratio was determined from its NMR spectrum.
32. H.W. Pinnick P. Beak R. Bittman E. Ciganek S. Hanessian L. Hegedus R.C. Kelly S.V. Ley L.E. Overman H.J. Reich C.J. Sih A.B. Smith III M. Uskovic Organic Reactions Vol. 38 1990 Wiley New York 665 and references therein
33. For review see: (b) R. Ballini, and M. Patrini Tetrahedron 60 2004 1017 1047
34. TBS, acetate and benzyl protecting groups were used.
35. M. Bartra, P. Romea, F. Urpi, and J. Vilarrasa Tetrahedron 46 1990 587 594
36. J. Darbowicz Synthesis 1980 125 126
37. R. Zimmer, U. Hain, M. Berndt, R. Gewald, and H.-U. Ressing Tetrahedron: Asymmetry 11 2000 879 887 and references cited therein
38. For recent reviews on ring closing metathesis see: (a) A. Fürstner Angew. Chem., Int. Ed. 39 2000 3013 3043
39. J. Prunet Angew. Chem., Int. Ed. 42 2003 2826 2830