A chemoenzymatic approach to the taxoid BC-substructure

Tetrahedron

Volumn 52, Issue 17, 1996, Pages 6215-6232

  Arseniyadis, Siméon ^a   Yashunsky, Dmitry V ^a   Muñoz Dorado, Manuel ^a   Brondi Alves, Rosemeire ^a   Wang, Qian ^a   Potier, Pierre ^a   Toupet, Loïc ^b  

^a CNRS   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE; TAXOID;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0029935501     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00270-0     Document Type: Article

References (48)

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2. Arseniyadis, S.; Yashunsky, D.V.; Muñoz-Dorado M.; Brondi Alves, R.; Toromanoff, E.; Toupet, L.; Potier, P. Tetrahedron Lett. 1993, 34, 4927-4930.
3. Note that in a more recent paper from this laboratory : Arseniyadis, S.; Wang, Q.; Yashunsky, D.V.; Kaoudi, T.; Brondi Alves, R.; Potier, P. Tetrahedron Lett. 1995, 36, 1633-1636, the (S)-absolute configuration of 2 was given as dextrorotatory, due to a typographical error, and was reported as (S)-(+)-2. The correct assignment is (S)-(-)-2.
4. For an excellent review see Boa, A.N.; Jenkins, P.R.; Lawrence, N.J. Contemporary Organic Synthesis 1994, 1. 47-75; For total syntheses of taxol see: Nicolaou, K.C.; Yang, Z.; Liu, J.J.; Ueno, H.; Nantermet, P.G.; Guy, R.K.; Claiborne, C.F.; Renaud, J,; Couladouros, E.A.; Paulvannan, K.; Sorensen, E.J. Nature 1994, 367, 630-634; Holton, R.A.; Somoza, C.; Kim, H.B.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1597-1600; Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
5. For an excellent review see Boa, A.N.; Jenkins, P.R.; Lawrence, N.J. Contemporary Organic Synthesis 1994, 1. 47-75; For total syntheses of taxol see: Nicolaou, K.C.; Yang, Z.; Liu, J.J.; Ueno, H.; Nantermet, P.G.; Guy, R.K.; Claiborne, C.F.; Renaud, J,; Couladouros, E.A.; Paulvannan, K.; Sorensen, E.J. Nature 1994, 367, 630-634; Holton, R.A.; Somoza, C.; Kim, H.B.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1597-1600; Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
6. For an excellent review see Boa, A.N.; Jenkins, P.R.; Lawrence, N.J. Contemporary Organic Synthesis 1994, 1. 47-75; For total syntheses of taxol see: Nicolaou, K.C.; Yang, Z.; Liu, J.J.; Ueno, H.; Nantermet, P.G.; Guy, R.K.; Claiborne, C.F.; Renaud, J,; Couladouros, E.A.; Paulvannan, K.; Sorensen, E.J. Nature 1994, 367, 630-634; Holton, R.A.; Somoza, C.; Kim, H.B.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1597-1600; Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
7. For an excellent review see Boa, A.N.; Jenkins, P.R.; Lawrence, N.J. Contemporary Organic Synthesis 1994, 1. 47-75; For total syntheses of taxol see: Nicolaou, K.C.; Yang, Z.; Liu, J.J.; Ueno, H.; Nantermet, P.G.; Guy, R.K.; Claiborne, C.F.; Renaud, J,; Couladouros, E.A.; Paulvannan, K.; Sorensen, E.J. Nature 1994, 367, 630-634; Holton, R.A.; Somoza, C.; Kim, H.B.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1597-1600; Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
8. For the construction of taxoid BC (6+8) ring system see: Swindell, C.S.; deSolms, S.J. Tetrahedron Lett. 1984, 25, 3801-3804; Swindell, C.S.; Patel, B.P.; deSolms, S.J.; Springer, J.P. J. Org. Chem. 1987, 52, 2346-2355; Swindell, C.S.; Patel, B.P. J. Org. Chem. 1990, 55, 3-5 ; Kojima, T.; Inouye, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1985 , 58, 1738-1740 ; Wender, P.A.; Ihle, N.C. Tetrahedron Lett. 1987, 25, 2451-2454 ; Wender, P.A.; Correia, C.R.D. J. Am. Chem. Soc. 1987, 709, 2523-2525.
9. For the construction of taxoid BC (6+8) ring system see: Swindell, C.S.; deSolms, S.J. Tetrahedron Lett. 1984, 25, 3801-3804; Swindell, C.S.; Patel, B.P.; deSolms, S.J.; Springer, J.P. J. Org. Chem. 1987, 52, 2346-2355; Swindell, C.S.; Patel, B.P. J. Org. Chem. 1990, 55, 3-5 ; Kojima, T.; Inouye, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1985 , 58, 1738-1740 ; Wender, P.A.; Ihle, N.C. Tetrahedron Lett. 1987, 25, 2451-2454 ; Wender, P.A.; Correia, C.R.D. J. Am. Chem. Soc. 1987, 709, 2523-2525.
10. For the construction of taxoid BC (6+8) ring system see: Swindell, C.S.; deSolms, S.J. Tetrahedron Lett. 1984, 25, 3801-3804; Swindell, C.S.; Patel, B.P.; deSolms, S.J.; Springer, J.P. J. Org. Chem. 1987, 52, 2346-2355; Swindell, C.S.; Patel, B.P. J. Org. Chem. 1990, 55, 3-5 ; Kojima, T.; Inouye, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1985 , 58, 1738-1740 ; Wender, P.A.; Ihle, N.C. Tetrahedron Lett. 1987, 25, 2451-2454 ; Wender, P.A.; Correia, C.R.D. J. Am. Chem. Soc. 1987, 709, 2523-2525.
11. For the construction of taxoid BC (6+8) ring system see: Swindell, C.S.; deSolms, S.J. Tetrahedron Lett. 1984, 25, 3801-3804; Swindell, C.S.; Patel, B.P.; deSolms, S.J.; Springer, J.P. J. Org. Chem. 1987, 52, 2346-2355; Swindell, C.S.; Patel, B.P. J. Org. Chem. 1990, 55, 3-5 ; Kojima, T.; Inouye, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1985 , 58, 1738-1740 ; Wender, P.A.; Ihle, N.C. Tetrahedron Lett. 1987, 25, 2451-2454 ; Wender, P.A.; Correia, C.R.D. J. Am. Chem. Soc. 1987, 709, 2523-2525.
12. For the construction of taxoid BC (6+8) ring system see: Swindell, C.S.; deSolms, S.J. Tetrahedron Lett. 1984, 25, 3801-3804; Swindell, C.S.; Patel, B.P.; deSolms, S.J.; Springer, J.P. J. Org. Chem. 1987, 52, 2346-2355; Swindell, C.S.; Patel, B.P. J. Org. Chem. 1990, 55, 3-5 ; Kojima, T.; Inouye, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1985 , 58, 1738-1740 ; Wender, P.A.; Ihle, N.C. Tetrahedron Lett. 1987, 25, 2451-2454 ; Wender, P.A.; Correia, C.R.D. J. Am. Chem. Soc. 1987, 709, 2523-2525.
13. For the construction of taxoid BC (6+8) ring system see: Swindell, C.S.; deSolms, S.J. Tetrahedron Lett. 1984, 25, 3801-3804; Swindell, C.S.; Patel, B.P.; deSolms, S.J.; Springer, J.P. J. Org. Chem. 1987, 52, 2346-2355; Swindell, C.S.; Patel, B.P. J. Org. Chem. 1990, 55, 3-5 ; Kojima, T.; Inouye, Y.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1985 , 58, 1738-1740 ; Wender, P.A.; Ihle, N.C. Tetrahedron Lett. 1987, 25, 2451-2454 ; Wender, P.A.; Correia, C.R.D. J. Am. Chem. Soc. 1987, 709, 2523-2525.
14. Baldwin, J.E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J.E.; Lusch, M.J. Tetrahedron 1982, 38, 2939-2947; Beckwith, A.L.J.; Schiesser, C.H. Tetrahedron 1985,47, 3925-3941.
15. Baldwin, J.E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J.E.; Lusch, M.J. Tetrahedron 1982, 38, 2939-2947; Beckwith, A.L.J.; Schiesser, C.H. Tetrahedron 1985,47, 3925-3941.
16. Baldwin, J.E. J. Chem. Soc., Chem. Commun. 1976, 734-736; Baldwin, J.E.; Lusch, M.J. Tetrahedron 1982, 38, 2939-2947; Beckwith, A.L.J.; Schiesser, C.H. Tetrahedron 1985,47, 3925-3941.
17. Heathcock, C.H. In Asymmetric Synthesis, Morrison, J.D., Ed. Academic Press Inc.: New York, 1984, vol.3, 111-212.
18. For an elegant synthesis of the taxoid B-ring by oxidative ring cleavage see: Blechert, S.; Müller R.; Beitzel, M. Tetrahedron 1992, 48, 6953-6964.
19. Cyclotene, commercially available from Aldrich, is a principal component of coffee aroma and maple syrup, widely used as an artificial flavor in various food items for its caramel-like flavor.
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21. 2 column chromatography, but losing half of the weight at this stage was obviously impractical.
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24. Conjugate addition of organometallic reagents to enantiomerically pure arylsulfinyl cyclopentenones: Possner, G.H.; Mallamo, J.P.; Hulce, M.; Frye, L.L. J. Am. Chem. Soc. 1982, 104, 4180-4185; Chromatographic resolution of key intermediates prepared from 1-menthol: Taber, D.F.; Saleh, S.A.; Korsmeyer, R.W. J. Org. Chem. 1980, 45, 4699-4702; Enantioselective cyclization using chiral Rhodium (I)-complex: Wu, X-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927-5930.
25. Curvularia lunata, Aspergillus niger, Aspergillus ochraceous, Aspergillus alliacens, Geotrichum candidum, Baker's yeast were used to achieve enantioselective microbial reduction, but all proved unsuccessful.
26. Although several intermediates of our synthetic scheme such as 5, 6, 16, 17 and others were reasonable candidates for an enzyme catalyzed resolution, for obvious reasons, we focused on intermediates before the aldol coupling.
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28. The selection of this lipases (Liver Acetone Powder, Sigma) was based on our previous results: Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron 1994, 50, 8399-8426.
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34. Birch, A.J. J.Chem.Soc. 1950, 1551-1556; Birch, A.J.; Slobbe, J. Aust. J. Chem. 1977, 30, 1045-1049; Van Bekkum, H.; Van Den Bosch, C.B.; Van Minnen-Pathuis, G.; De Mos, J.C.; Van Wijk, A.M. Rec. Trav. Chim. Pays-Bas 1971, 90, 137-149.
35. Birch, A.J. J.Chem.Soc. 1950, 1551-1556; Birch, A.J.; Slobbe, J. Aust. J. Chem. 1977, 30, 1045-1049; Van Bekkum, H.; Van Den Bosch, C.B.; Van Minnen-Pathuis, G.; De Mos, J.C.; Van Wijk, A.M. Rec. Trav. Chim. Pays-Bas 1971, 90, 137-149.
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37. Zimmerman, H.E.; Traxler, M.D. J. Am. Chem. Soc. 1957, 79, 1920-1923. The threo (erythro) Zimmerman-Traxler transition states account well for the observed simple diastereoselection and π-facial selectivity. A transition state rationale as well as the hydrogen bonded conformations (around 3 Kcal/mol lower in energy then the lowest energy non-hydrogen bonded conformera) of major (4M) and minor (4m) threo aldols as determined by molecular mechanics calculations is shown below Matrix Presented
38. 3)+, 94], 307 (61), 217 (20), 201 (21). The structures of i, ii, iii were established by diagnostic n.O.e. experiments as depicted below: Matrix Presented
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43. The desired enone 5 initially obtained in 67% yield was accompanied with its corresponding allylic alcohol which was reoxidized with PDC in dichloromethane to give an additional 8% recovery of 5.
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