Synthesis of a butyrolactone precursor of an algae nonaether from an enantiopure glycol obtained by Hoppe's chemistry

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 1023-1030

  Menges, Markus ^a,b   Brückner, Reinhard ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b BASF SE   (Germany)

Author keywords

Carbamates, functionalization of; Lactones from dienes; Neighboring group effects, in reduction; Polyethers from Scytonema or Tolypothrix; Reduction, diastereoselective

Indexed keywords

EID: 0008496147     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199806)1998:6<1023::AID-EJOC1023>3.0.CO;2-3     Document Type: Article

References (68)

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2. T. Oishi, T. Nakata, Synthesis 1990, 635-645; S. D. Rychnovsky. Chem. Rev. 1995, 95, 2021-2040.
3. S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Analogous results - which, however, do not concern the synthesis of type-3 1,3-diols - are described by S. Hanessian, P. J Murray, Tetrahedron 1987, 43, 5055-5072 and reviewed by S. Hanessian, Aldrichimica Acta 1989, 22, 3-15.
4. S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Analogous results - which, however, do not concern the synthesis of type-3 1,3-diols - are described by S. Hanessian, P. J Murray, Tetrahedron 1987, 43, 5055-5072 and reviewed by S. Hanessian, Aldrichimica Acta 1989, 22, 3-15.
5. S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Analogous results - which, however, do not concern the synthesis of type-3 1,3-diols - are described by S. Hanessian, P. J Murray, Tetrahedron 1987, 43, 5055-5072 and reviewed by S. Hanessian, Aldrichimica Acta 1989, 22, 3-15.
6. [3a] H. Priepke, Dissertation, Universität Würzburg, 1993.
7. [3b] M. Menges, R. Brückner, Synlett 1993, 901-905.
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13. Isolation from Tolypothrix: J. S. Mynderse, R. E. Moore, Phytochemistry 1979, 18, 1181-1183; isolation from Scytonema. Y Mori, Y. Kohchi, M. Suzuki, S. Carmeli, R. E. Moore, G. M L. Patterson, J. Org. Chem. 1991, 56, 631-637.
14. Isolation from Tolypothrix: J. S. Mynderse, R. E. Moore, Phytochemistry 1979, 18, 1181-1183; isolation from Scytonema. Y Mori, Y. Kohchi, M. Suzuki, S. Carmeli, R. E. Moore, G. M L. Patterson, J. Org. Chem. 1991, 56, 631-637.
15. Total syntheses of the pentaether analog of 7: [7a] Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem 1991, 56, 631-637; ref. [5a-c]. Formal total synthesis: [7b] T. Makata, T Suenaga, T. Oishi. Tetrahedron Lett. 1989, 30, 6525-6528 in combination with [7c] T. Nakata, T. Suenaga, K. Nakashima. T. Oishi, Tetrahedron Lett. 1989, 30, 6529-6532. Total synthesis of the hexaether analog of 7: ref. [7a]. Total syntheses of the octaether analog of 7: ref. [7a]. - [7d] Z. Wang, D. Deschênes, J. Am Chem. Soc. 1992. 114, 1090-1091. Total syntheses of 7: ref. [7a][7c]. - [7e] Y. Mori, Y. Kohchi, T. Ota, M. Suzuki, Tetrahedron Lett 1990, 31, 2915-2916. - Total synthesis of the decaether analog of 7: [7f] S. D. Rychnovsky, G. Griesgraber, J. Org. Chem. 1992, 57, 1559-1563.
16. Total syntheses of the pentaether analog of 7: [7a] Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem 1991, 56, 631-637; ref. [5a-c]. Formal total synthesis: [7b] T. Makata, T Suenaga, T. Oishi. Tetrahedron Lett. 1989, 30, 6525-6528 in combination with [7c] T. Nakata, T. Suenaga, K. Nakashima. T. Oishi, Tetrahedron Lett. 1989, 30, 6529-6532. Total synthesis of the hexaether analog of 7: ref. [7a]. Total syntheses of the octaether analog of 7: ref. [7a]. - [7d] Z. Wang, D. Deschênes, J. Am Chem. Soc. 1992. 114, 1090-1091. Total syntheses of 7: ref. [7a][7c]. - [7e] Y. Mori, Y. Kohchi, T. Ota, M. Suzuki, Tetrahedron Lett 1990, 31, 2915-2916. - Total synthesis of the decaether analog of 7: [7f] S. D. Rychnovsky, G. Griesgraber, J. Org. Chem. 1992, 57, 1559-1563.
17. Total syntheses of the pentaether analog of 7: [7a] Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem 1991, 56, 631-637; ref. [5a-c]. Formal total synthesis: [7b] T. Makata, T Suenaga, T. Oishi. Tetrahedron Lett. 1989, 30, 6525-6528 in combination with [7c] T. Nakata, T. Suenaga, K. Nakashima. T. Oishi, Tetrahedron Lett. 1989, 30, 6529-6532. Total synthesis of the hexaether analog of 7: ref. [7a]. Total syntheses of the octaether analog of 7: ref. [7a]. - [7d] Z. Wang, D. Deschênes, J. Am Chem. Soc. 1992. 114, 1090-1091. Total syntheses of 7: ref. [7a][7c]. - [7e] Y. Mori, Y. Kohchi, T. Ota, M. Suzuki, Tetrahedron Lett 1990, 31, 2915-2916. - Total synthesis of the decaether analog of 7: [7f] S. D. Rychnovsky, G. Griesgraber, J. Org. Chem. 1992, 57, 1559-1563.
18. Total syntheses of the pentaether analog of 7: [7a] Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem 1991, 56, 631-637; ref. [5a-c]. Formal total synthesis: [7b] T. Makata, T Suenaga, T. Oishi. Tetrahedron Lett. 1989, 30, 6525-6528 in combination with [7c] T. Nakata, T. Suenaga, K. Nakashima. T. Oishi, Tetrahedron Lett. 1989, 30, 6529-6532. Total synthesis of the hexaether analog of 7: ref. [7a]. Total syntheses of the octaether analog of 7: ref. [7a]. - [7d] Z. Wang, D. Deschênes, J. Am Chem. Soc. 1992. 114, 1090-1091. Total syntheses of 7: ref. [7a][7c]. - [7e] Y. Mori, Y. Kohchi, T. Ota, M. Suzuki, Tetrahedron Lett 1990, 31, 2915-2916. - Total synthesis of the decaether analog of 7: [7f] S. D. Rychnovsky, G. Griesgraber, J. Org. Chem. 1992, 57, 1559-1563.
19. Total syntheses of the pentaether analog of 7: [7a] Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem 1991, 56, 631-637; ref. [5a-c]. Formal total synthesis: [7b] T. Makata, T Suenaga, T. Oishi. Tetrahedron Lett. 1989, 30, 6525-6528 in combination with [7c] T. Nakata, T. Suenaga, K. Nakashima. T. Oishi, Tetrahedron Lett. 1989, 30, 6529-6532. Total synthesis of the hexaether analog of 7: ref. [7a]. Total syntheses of the octaether analog of 7: ref. [7a]. - [7d] Z. Wang, D. Deschênes, J. Am Chem. Soc. 1992. 114, 1090-1091. Total syntheses of 7: ref. [7a][7c]. - [7e] Y. Mori, Y. Kohchi, T. Ota, M. Suzuki, Tetrahedron Lett 1990, 31, 2915-2916. - Total synthesis of the decaether analog of 7: [7f] S. D. Rychnovsky, G. Griesgraber, J. Org. Chem. 1992, 57, 1559-1563.
20. Total syntheses of the pentaether analog of 7: [7a] Y. Mori, Y. Kohchi, M. Suzuki, J. Org. Chem 1991, 56, 631-637; ref. [5a-c]. Formal total synthesis: [7b] T. Makata, T Suenaga, T. Oishi. Tetrahedron Lett. 1989, 30, 6525-6528 in combination with [7c] T. Nakata, T. Suenaga, K. Nakashima. T. Oishi, Tetrahedron Lett. 1989, 30, 6529-6532. Total synthesis of the hexaether analog of 7: ref. [7a]. Total syntheses of the octaether analog of 7: ref. [7a]. - [7d] Z. Wang, D. Deschênes, J. Am Chem. Soc. 1992. 114, 1090-1091. Total syntheses of 7: ref. [7a][7c]. - [7e] Y. Mori, Y. Kohchi, T. Ota, M. Suzuki, Tetrahedron Lett 1990, 31, 2915-2916. - Total synthesis of the decaether analog of 7: [7f] S. D. Rychnovsky, G. Griesgraber, J. Org. Chem. 1992, 57, 1559-1563.
21. [8a] 4-Step sequence for the conversion of S-glycidol into lactone 15: H. Priepke, S. Weigand, R. Brückner, Liebigs Ann. 1997, 1635-1644. - [8b] 8-step synthesis of the cnantiomer of 15 from L-glutamic acid: Step 1: U. Ravid. R. M. Silverstein, L. R. Smith, Tetrahedron 1978, 34, 1449-1452; step 2: C. Herdeis, Synthesis 1986, 232-233: step 3: S. Hanessian, P. J. Murray, Tetrahedron 1987, 43, 5055-5072; steps 4-8: S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Starting from D-glutamic acid the same sequence would furnish 15 but D-glutamic acid is very expensive.
22. [8a] 4-Step sequence for the conversion of S-glycidol into lactone 15: H. Priepke, S. Weigand, R. Brückner, Liebigs Ann. 1997, 1635-1644. - [8b] 8-step synthesis of the cnantiomer of 15 from L-glutamic acid: Step 1: U. Ravid. R. M. Silverstein, L. R. Smith, Tetrahedron 1978, 34, 1449-1452; step 2: C. Herdeis, Synthesis 1986, 232-233: step 3: S. Hanessian, P. J. Murray, Tetrahedron 1987, 43, 5055-5072; steps 4-8: S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Starting from D-glutamic acid the same sequence would furnish 15 but D-glutamic acid is very expensive.
23. [8a] 4-Step sequence for the conversion of S-glycidol into lactone 15: H. Priepke, S. Weigand, R. Brückner, Liebigs Ann. 1997, 1635-1644. - [8b] 8-step synthesis of the cnantiomer of 15 from L-glutamic acid: Step 1: U. Ravid. R. M. Silverstein, L. R. Smith, Tetrahedron 1978, 34, 1449-1452; step 2: C. Herdeis, Synthesis 1986, 232-233: step 3: S. Hanessian, P. J. Murray, Tetrahedron 1987, 43, 5055-5072; steps 4-8: S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Starting from D-glutamic acid the same sequence would furnish 15 but D-glutamic acid is very expensive.
24. [8a] 4-Step sequence for the conversion of S-glycidol into lactone 15: H. Priepke, S. Weigand, R. Brückner, Liebigs Ann. 1997, 1635-1644. - [8b] 8-step synthesis of the cnantiomer of 15 from L-glutamic acid: Step 1: U. Ravid. R. M. Silverstein, L. R. Smith, Tetrahedron 1978, 34, 1449-1452; step 2: C. Herdeis, Synthesis 1986, 232-233: step 3: S. Hanessian, P. J. Murray, Tetrahedron 1987, 43, 5055-5072; steps 4-8: S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Starting from D-glutamic acid the same sequence would furnish 15 but D-glutamic acid is very expensive.
25. [8a] 4-Step sequence for the conversion of S-glycidol into lactone 15: H. Priepke, S. Weigand, R. Brückner, Liebigs Ann. 1997, 1635-1644. - [8b] 8-step synthesis of the cnantiomer of 15 from L-glutamic acid: Step 1: U. Ravid. R. M. Silverstein, L. R. Smith, Tetrahedron 1978, 34, 1449-1452; step 2: C. Herdeis, Synthesis 1986, 232-233: step 3: S. Hanessian, P. J. Murray, Tetrahedron 1987, 43, 5055-5072; steps 4-8: S. Hanessian, S. P. Sahoo, P. J. Murray, Tetrahedron Lett. 1985, 26, 5631-5634. Starting from D-glutamic acid the same sequence would furnish 15 but D-glutamic acid is very expensive.
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41. Method: D Hoppe, F. Hintze, P. Tebben, Angew Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1424. - Reviews: D. Hoppe, F. Hintze, P. Tebben, M. Paetow, H. Ahrens, J. Schwerdtfeger, P. Sommerfeld, J. Haller, W. Guarnieri, S. Kolczewski, T. Hense, I. Hoppe, Pure Appl. Chem. 1994, 66, 1479-1486 ; D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
42. Method: D Hoppe, F. Hintze, P. Tebben, Angew Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1424. - Reviews: D. Hoppe, F. Hintze, P. Tebben, M. Paetow, H. Ahrens, J. Schwerdtfeger, P. Sommerfeld, J. Haller, W. Guarnieri, S. Kolczewski, T. Hense, I. Hoppe, Pure Appl. Chem. 1994, 66, 1479-1486 ; D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
43. Method: D Hoppe, F. Hintze, P. Tebben, Angew Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1424. - Reviews: D. Hoppe, F. Hintze, P. Tebben, M. Paetow, H. Ahrens, J. Schwerdtfeger, P. Sommerfeld, J. Haller, W. Guarnieri, S. Kolczewski, T. Hense, I. Hoppe, Pure Appl. Chem. 1994, 66, 1479-1486 ; D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
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46. Reagent: M. Schlosser, T. Jenny, Y. Guggisbcrg, Synlett 1990, 704.
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56. Method: K. Narasaka, F.-C. Pai, Chem. Lett. 1980, 1415-1418; K. Narasaka, F.-C. Pai, Tetrahedron 1984, 40, 2233-2238; K.-M. Chen, G. E. Hardtmann, K. Prasad, O. Repic, M. J. Shapiro, Tetrahedron Lett. 1987, 26, 2951-2954; K.-M. Chen, K. G. Gunderson, G. E. Hardtmann, K. Prasad, O. Repic, M. J. Shapiro, Chem. Lett. 1987, 1923-1926.
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61. 4NI: R. Kuhn, I. Löw, H. Trischmann, Chem. Ber. 1957, 90, 203-218; L. Van Hijfte, R. D Little, J. Org. Chem. 1985, 50, 3940-3942.
62. Reaction with O-benzyl trichloroacetimidate: P. Eckenberg, U. Groth, T. Huhn, N. Richter, C. Schmeck, Tetrahedron 1993, 49, 1619-1624.
63. 2/BnBr: M. Yamashita, Synthesis 1977, 803.
64. 2, -12°C, 1 d; 50%; cf. Experimental Section].
65. Procedure; J. E. T. Corrie, J. Chem. Soc. Perkin Trans, 1, 1993, 2161-2166. - For a review of monofunctionalizations of Snacetals of glycols cf. S. David, S. Hanessian, Tetrahedron 1985, 41- 643-663.
66. Procedure; J. E. T. Corrie, J. Chem. Soc. Perkin Trans, 1, 1993, 2161-2166. - For a review of monofunctionalizations of Snacetals of glycols cf. S. David, S. Hanessian, Tetrahedron 1985, 41- 643-663.
67. procedure: S. Takano, M. Yonaga, K. Ogasawara, Synthesis 1981, 265-266.
68. J. Suffert, J. Org. Chem. 1989, 54, 509-510.