Synthesis of (+)-ginnol, a type R(long)-CH(OH)-R'(long) alcohol, by an asymmetric β,γ-unsaturated ester→γ-butyrolactone conversion

Tetrahedron

Volumn 54, Issue 38, 1998, Pages 11471-11480

  Berkenbusch, Thilo ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alcohols; Asymmetric Synthesis; Lactones; Osmylation

Indexed keywords

ALCOHOL; ESTER; GAMMA BUTYROLACTONE; GINNOL; UNCLASSIFIED DRUG;

ARTICLE; DEHYDRATION; ENANTIOMER; HYDROXYLATION; ISOMERISM; PLANT; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032541590     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00688-7     Document Type: Article

References (34)

1. [1] Reviews: Ogliaruso MA, Wolfe JF. Synthesis of Lactones and Lactams (Updates to the Chemistry of Functional Groups), Wiley, Chichester, 1993. Knight DW. Contemp. Org. Synth. 1994, 1, 287-315. Mulzer J. Comprehensive Organic Group Transformations, Vol. 5 (Katritzky AR; Meth-Cohn O, Rees CW, Eds.), Elsevier Science, Oxford, 1995, pp. 121-180. Hoppe R, Scharf H-D. Synthesis 1995, 1447-1464. Cardillo G, Orena M. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4698-4817. Doyle MP. Aldrichim. Acta 1996, 29, 3-11.
2. [1] Reviews: Ogliaruso MA, Wolfe JF. Synthesis of Lactones and Lactams (Updates to the Chemistry of Functional Groups), Wiley, Chichester, 1993. Knight DW. Contemp. Org. Synth. 1994, 1, 287-315. Mulzer J. Comprehensive Organic Group Transformations, Vol. 5 (Katritzky AR; Meth-Cohn O, Rees CW, Eds.), Elsevier Science, Oxford, 1995, pp. 121-180. Hoppe R, Scharf H-D. Synthesis 1995, 1447-1464. Cardillo G, Orena M. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4698-4817. Doyle MP. Aldrichim. Acta 1996, 29, 3-11.
3. [1] Reviews: Ogliaruso MA, Wolfe JF. Synthesis of Lactones and Lactams (Updates to the Chemistry of Functional Groups), Wiley, Chichester, 1993. Knight DW. Contemp. Org. Synth. 1994, 1, 287-315. Mulzer J. Comprehensive Organic Group Transformations, Vol. 5 (Katritzky AR; Meth-Cohn O, Rees CW, Eds.), Elsevier Science, Oxford, 1995, pp. 121-180. Hoppe R, Scharf H-D. Synthesis 1995, 1447-1464. Cardillo G, Orena M. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4698-4817. Doyle MP. Aldrichim. Acta 1996, 29, 3-11.
4. [1] Reviews: Ogliaruso MA, Wolfe JF. Synthesis of Lactones and Lactams (Updates to the Chemistry of Functional Groups), Wiley, Chichester, 1993. Knight DW. Contemp. Org. Synth. 1994, 1, 287-315. Mulzer J. Comprehensive Organic Group Transformations, Vol. 5 (Katritzky AR; Meth-Cohn O, Rees CW, Eds.), Elsevier Science, Oxford, 1995, pp. 121-180. Hoppe R, Scharf H-D. Synthesis 1995, 1447-1464. Cardillo G, Orena M. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4698-4817. Doyle MP. Aldrichim. Acta 1996, 29, 3-11.
5. [1] Reviews: Ogliaruso MA, Wolfe JF. Synthesis of Lactones and Lactams (Updates to the Chemistry of Functional Groups), Wiley, Chichester, 1993. Knight DW. Contemp. Org. Synth. 1994, 1, 287-315. Mulzer J. Comprehensive Organic Group Transformations, Vol. 5 (Katritzky AR; Meth-Cohn O, Rees CW, Eds.), Elsevier Science, Oxford, 1995, pp. 121-180. Hoppe R, Scharf H-D. Synthesis 1995, 1447-1464. Cardillo G, Orena M. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4698-4817. Doyle MP. Aldrichim. Acta 1996, 29, 3-11.
6. [1] Reviews: Ogliaruso MA, Wolfe JF. Synthesis of Lactones and Lactams (Updates to the Chemistry of Functional Groups), Wiley, Chichester, 1993. Knight DW. Contemp. Org. Synth. 1994, 1, 287-315. Mulzer J. Comprehensive Organic Group Transformations, Vol. 5 (Katritzky AR; Meth-Cohn O, Rees CW, Eds.), Elsevier Science, Oxford, 1995, pp. 121-180. Hoppe R, Scharf H-D. Synthesis 1995, 1447-1464. Cardillo G, Orena M. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4698-4817. Doyle MP. Aldrichim. Acta 1996, 29, 3-11.
7. [2] Harcken C, Brückner R. Angew. Chem. 1997, 109, 2866-2868; Angew. Chem. Int. Ed. Engl. 1997, 36, 2750-2752. This reaction type had been described albeit never exploited: Wang ZM, Zhang XL, Sharpless KB, Sinha SC, Sinha-Bagchi A, Keinan E. Tetrahedron Lett. 1992, 33, 6407-6410. Miyazaki Y, Hotta H, Sato F. Tetrahedron Lett. 1994, 35, 4389-4392.
8. [2] Harcken C, Brückner R. Angew. Chem. 1997, 109, 2866-2868; Angew. Chem. Int. Ed. Engl. 1997, 36, 2750-2752. This reaction type had been described albeit never exploited: Wang ZM, Zhang XL, Sharpless KB, Sinha SC, Sinha-Bagchi A, Keinan E. Tetrahedron Lett. 1992, 33, 6407-6410. Miyazaki Y, Hotta H, Sato F. Tetrahedron Lett. 1994, 35, 4389-4392.
9. [2] Harcken C, Brückner R. Angew. Chem. 1997, 109, 2866-2868; Angew. Chem. Int. Ed. Engl. 1997, 36, 2750-2752. This reaction type had been described albeit never exploited: Wang ZM, Zhang XL, Sharpless KB, Sinha SC, Sinha-Bagchi A, Keinan E. Tetrahedron Lett. 1992, 33, 6407-6410. Miyazaki Y, Hotta H, Sato F. Tetrahedron Lett. 1994, 35, 4389-4392.
10. [2] Harcken C, Brückner R. Angew. Chem. 1997, 109, 2866-2868; Angew. Chem. Int. Ed. Engl. 1997, 36, 2750-2752. This reaction type had been described albeit never exploited: Wang ZM, Zhang XL, Sharpless KB, Sinha SC, Sinha-Bagchi A, Keinan E. Tetrahedron Lett. 1992, 33, 6407-6410. Miyazaki Y, Hotta H, Sato F. Tetrahedron Lett. 1994, 35, 4389-4392.
11. [3] Harcken C, Rank E (in part), Brückner R. Chem. Eur. J. 1998, 4, in the press.
12. [4] Berkenbusch T, Brückner, R. Tetrahedron 1998, 54, 11461-11470.
13. [5] Berkenbusch T. Diplomarbeit, Universität Göttingen, 1998. Braukmüller S. Diplomarbeit, Universität Göttingen, 1998.
14. [5] Berkenbusch T. Diplomarbeit, Universität Göttingen, 1998. Braukmüller S. Diplomarbeit, Universität Göttingen, 1998.
15. [6] Sharpless KB, Amberg W, Bennani YL, Crispino GA, Hartung J, Jeong K-S, Kwong H-L, Morikawa K, Wang Z-M, Xu D, Zhang X-L. J. Org. Chem. 1992, 57, 2768-2771.
16. [7] Reviews: Lohray BB. Tetrahedron: Asymmetry 1992, 3, 1317-1349. Johnson RA, Sharpless KB. Asymmetric Catalysis in Organic Synthesis (Edt.: Ojima I), VCH, New York, 1993, 227-272. Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994, 94, 2483-2547. Poli G, Scolastico C. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4547-4598.
17. [7] Reviews: Lohray BB. Tetrahedron: Asymmetry 1992, 3, 1317-1349. Johnson RA, Sharpless KB. Asymmetric Catalysis in Organic Synthesis (Edt.: Ojima I), VCH, New York, 1993, 227-272. Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994, 94, 2483-2547. Poli G, Scolastico C. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4547-4598.
18. [7] Reviews: Lohray BB. Tetrahedron: Asymmetry 1992, 3, 1317-1349. Johnson RA, Sharpless KB. Asymmetric Catalysis in Organic Synthesis (Edt.: Ojima I), VCH, New York, 1993, 227-272. Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994, 94, 2483-2547. Poli G, Scolastico C. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4547-4598.
19. [7] Reviews: Lohray BB. Tetrahedron: Asymmetry 1992, 3, 1317-1349. Johnson RA, Sharpless KB. Asymmetric Catalysis in Organic Synthesis (Edt.: Ojima I), VCH, New York, 1993, 227-272. Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994, 94, 2483-2547. Poli G, Scolastico C. Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e (Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, Eds.), Thieme, Stuttgart, 1995, pp. 4547-4598.
20. [8] Isolation and incorrect constitution: Sando CE. J. Biol. Chem. 1923, 56, 457-468 (Chem. Abs. 1924, 18, 1003). Correct constitution: Chibnall AC, Piper SH, Pollard A, Smith JAB, Williams EF. Biochem. J. 1931, 25, 2095-2110. Configuration: Kusumi T, Takahashi H, Hashimoto T, Kan Y, Asakawa Y. Chem. Lett. 1994, 1093-1094. Kouda K, Kusumi T, Ping X, Kan Y, Hashimoto T, Asakawa Y. Tetrahedron Lett. 1996, 37, 4541-4544.
21. [8] Isolation and incorrect constitution: Sando CE. J. Biol. Chem. 1923, 56, 457-468 (Chem. Abs. 1924, 18, 1003). Correct constitution: Chibnall AC, Piper SH, Pollard A, Smith JAB, Williams EF. Biochem. J. 1931, 25, 2095-2110. Configuration: Kusumi T, Takahashi H, Hashimoto T, Kan Y, Asakawa Y. Chem. Lett. 1994, 1093-1094. Kouda K, Kusumi T, Ping X, Kan Y, Hashimoto T, Asakawa Y. Tetrahedron Lett. 1996, 37, 4541-4544.
22. [8] Isolation and incorrect constitution: Sando CE. J. Biol. Chem. 1923, 56, 457-468 (Chem. Abs. 1924, 18, 1003). Correct constitution: Chibnall AC, Piper SH, Pollard A, Smith JAB, Williams EF. Biochem. J. 1931, 25, 2095-2110. Configuration: Kusumi T, Takahashi H, Hashimoto T, Kan Y, Asakawa Y. Chem. Lett. 1994, 1093-1094. Kouda K, Kusumi T, Ping X, Kan Y, Hashimoto T, Asakawa Y. Tetrahedron Lett. 1996, 37, 4541-4544.
23. [8] Isolation and incorrect constitution: Sando CE. J. Biol. Chem. 1923, 56, 457-468 (Chem. Abs. 1924, 18, 1003). Correct constitution: Chibnall AC, Piper SH, Pollard A, Smith JAB, Williams EF. Biochem. J. 1931, 25, 2095-2110. Configuration: Kusumi T, Takahashi H, Hashimoto T, Kan Y, Asakawa Y. Chem. Lett. 1994, 1093-1094. Kouda K, Kusumi T, Ping X, Kan Y, Hashimoto T, Asakawa Y. Tetrahedron Lett. 1996, 37, 4541-4544.
24. [9] a) Jetter R, Riederer M. Planta 1994, 195, 257-270.
25. b) Fuhrhop J-H, Bedurke T, Hahn A, Grund S, Gatzmann J, Riederer M. Angew. Chem. 1994, 106, 351-353; Angew. Chem. Int. Edn. Engl. 1994, 33, 350.
26. b) Fuhrhop J-H, Bedurke T, Hahn A, Grund S, Gatzmann J, Riederer M. Angew. Chem. 1994, 106, 351-353; Angew. Chem. Int. Edn. Engl. 1994, 33, 350.
27. [10] Procedure: Ragoussis N. Tetrahedron Lett. 1987, 28, 93-96.
28. [11] Still WC, Kahn M, Mitra A. J. Org. Chem 1978, 43, 2923-2925.
29. [12] Procedure: Yamanaka H, Yokoyama M, Sakamoto T, Shiraishi T, Sagi M, Mizugaki M. Heterocycles 1983, 20, 1541-1544.
30. [13] Procedure: Krief A, Dumont W, Pasau P, Lecomte P. Tetrahedron 1989, 45, 3039-3050.
31. 3 [15a]).
32. [15] a) Schwink L, Knochel P. Tetrahedron Lett. 1994, 35, 9007-9010.
33. b) Langer F, Schwink L, Devasagayaraj A, Chavant P-Y, Knochel P. J. Org. Chem. 1996, 61, 8229-8243.
34. [16] Beckmann S, Schühle H. Z. Naturforsch. 1968, 23b, 471-473.