Total synthesis of (+)-pinitol

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3535-3544

  Aceña, José Luis ^a   Arjona, Odón ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; INOSITOL DERIVATIVE; SULFONE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030561497     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00461-2     Document Type: Article

References (30)

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6. For reviews, see: b) Woo, S.; Keay, B. A. Synthesis 1996, 669.
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12. c) Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
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14. 7. Compounds 7 and 8 constitute challenging targets in Organic Synthesis due to their promising anticancer and antiviral properties, in addition to their low natural abundance. For their total synthesis, see: racemic pancratistatin: a) Danishefsky, S. J.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829.
15. Optically active: b) Tian, X.; Hudlicky, T.; Könisberger, K. J. Am. Chem. Soc. 1995, 117, 3643.
16. c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143.
17. Optically active 7-deoxypancratistatin: d) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289.
18. e) Tian, X.; Maurya, R.; Könisberger, K.; Hudlicky, T. Synlett 1995, 1125.
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21. b) Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
22. For the preparation of (±)-pinitol, see: c) Carless, H. A. J.; Billinge, J. R.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 3113.
23. 4NI; in 62% overall yield.
24. 2 or s-BuLi, variable amounts of starting material were recovered. On the other hand, the reaction with LDA afforded (+)-5 as the major product.
25. 12. McCarthy, J. R.; Huber, E. W.; Le, T.-B.; Laskovics, F. M.; Matthews, D. P. Tetrahedron 1996, 52, 45
26. 13. Direct substitution onto the triflate derived of 15 led to aromatization products.
27. 14. Mirsadeghi, S.; Rickborn, B. J. Org. Chem. 1985, 50, 4340.
28. 15. For an analogous process, see: Jung, M. E.; Truc, V. C. Tetrahedron Lett. 1988, 29, 6059 and references cited therein.
29. 16. a) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J. Tetrahedron Lett. 1991, 32, 7309.
30. b) Arjona, O.; Candilejo, A.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J. J. Org. Chem. 1992, 57, 6097.