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Volumn , Issue 14, 2002, Pages 1993-2012

Oxabicyclo[3.2.1]oct-6-enes as templates for the stereoselective synthesis of polypropionates: Total synthesis of callystatin a and C19-epi-callystatin A

Author keywords

Asymmetric synthesis; Natural products; Ring opening; Stereoselectivity; Total synthesis

Indexed keywords

ORGANIC COMPOUNDS;

EID: 0036400537     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34386     Document Type: Article
Times cited : (55)

References (95)
  • 26
    • 0035815143 scopus 로고    scopus 로고
    • For the use [2.2.1]oxabicycles as templates for polypropionate tetrads, see: (a) Arjona, O.; Menchaca, R.; Plumet, J. J. Org. Chem. 2001, 66, 2400. (b) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron 2001, 57, 6751. (c) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 6753. (d) Acena, J. L.; Arjona, O.; Leon, M.; Plumet, J. Tetrahedron Lett. 1996, 37, 8957.
    • (2001) J. Org. Chem. , vol.66 , pp. 2400
    • Arjona, O.1    Menchaca, R.2    Plumet, J.3
  • 27
    • 0035974275 scopus 로고    scopus 로고
    • For the use [2.2.1]oxabicycles as templates for polypropionate tetrads, see: (a) Arjona, O.; Menchaca, R.; Plumet, J. J. Org. Chem. 2001, 66, 2400. (b) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron 2001, 57, 6751. (c) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 6753. (d) Acena, J. L.; Arjona, O.; Leon, M.; Plumet, J. Tetrahedron Lett. 1996, 37, 8957.
    • (2001) Tetrahedron , vol.57 , pp. 6751
    • Arjona, O.1    Menchaca, R.2    Plumet, J.3
  • 28
    • 0032505257 scopus 로고    scopus 로고
    • For the use [2.2.1]oxabicycles as templates for polypropionate tetrads, see: (a) Arjona, O.; Menchaca, R.; Plumet, J. J. Org. Chem. 2001, 66, 2400. (b) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron 2001, 57, 6751. (c) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 6753. (d) Acena, J. L.; Arjona, O.; Leon, M.; Plumet, J. Tetrahedron Lett. 1996, 37, 8957.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6753
    • Arjona, O.1    Menchaca, R.2    Plumet, J.3
  • 29
    • 0030566783 scopus 로고    scopus 로고
    • For the use [2.2.1]oxabicycles as templates for polypropionate tetrads, see: (a) Arjona, O.; Menchaca, R.; Plumet, J. J. Org. Chem. 2001, 66, 2400. (b) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron 2001, 57, 6751. (c) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 6753. (d) Acena, J. L.; Arjona, O.; Leon, M.; Plumet, J. Tetrahedron Lett. 1996, 37, 8957.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8957
    • Acena, J.L.1    Arjona, O.2    Leon, M.3    Plumet, J.4
  • 58
    • 0001753657 scopus 로고
    • [4 + 3] cycloaddtions
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, Chapter 5.1
    • For reviews on [4 + 3] cycloadditions reactions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloaddtions, In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chapter 5.1, 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 593
    • Hosomi, A.1    Tominaga, Y.2
  • 59
    • 0001523555 scopus 로고
    • For reviews on [4 + 3] cycloadditions reactions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloaddtions, In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chapter 5.1, 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
    • (1986) Tetrahedron , vol.42 , pp. 4611
    • Mann, J.1
  • 60
    • 0002108811 scopus 로고
    • For reviews on [4 + 3] cycloadditions reactions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloaddtions, In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chapter 5.1, 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 1
    • Hoffmann, H.M.R.1
  • 61
    • 0000400239 scopus 로고
    • For reviews on [4 + 3] cycloadditions reactions, see: (a) Hosomi, A.; Tominaga, Y. [4 + 3] Cycloaddtions, In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chapter 5.1, 593. (b) Mann, J. Tetrahedron 1986, 42, 4611. (c) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
    • (1983) Org. React. , vol.29 , pp. 163
    • Noyori, R.1    Hayakawa, Y.2
  • 72
    • 85088722349 scopus 로고    scopus 로고
    • note
    • 12a.35
  • 73
    • 2142835111 scopus 로고    scopus 로고
    • note
    • Alternatively, diol 27 could also be prepared from intermediate 19 (Scheme 19).
  • 76
    • 0000810296 scopus 로고    scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (2001) Org. Lett. , vol.3 , pp. 3041
    • De Luca, L.1    Giacomelli, G.2    Porcheddu, A.3
  • 77
    • 0001097669 scopus 로고    scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (1996) J. Org. Chem. , vol.61 , pp. 7452
    • Einhorn, J.1    Einhorn, C.2    Ratajczak, F.3    Pierre, J.-L.4
  • 78
    • 84988109288 scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (1986) Synthesis , pp. 774
    • Nakano, T.1    Terada, T.2    Ishii, Y.3    Ogawa, M.4
  • 79
    • 0001495283 scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 1605
    • Tomioka, H.1    Takai, K.2    Oshima, K.3    Nozaki, H.4
  • 80
    • 0001602420 scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3964
    • Lansbury, P.T.1    Hangauer, D.G.2    Vacca, J.P.3
  • 81
    • 0017069616 scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 3379
    • Ketchmer, R.A.1    Thompson, W.J.2
  • 82
    • 0015896342 scopus 로고
    • There are relatively few examples of the selective oxidation of a primary alcohol in the presence of a secondary alcohol. For examples, see: (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452. (c) Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774. (d) Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605. (e) Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. (f) Ketchmer, R. A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379. (g) Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 14, 3899.
    • (1973) Tetrahedron Lett. , vol.14 , pp. 3899
    • Fried, J.1    Sih, J.C.2
  • 86
    • 85088719325 scopus 로고    scopus 로고
    • note
    • 2 allylic oxidation in approximately 4% yield. This material could be recycled by stirring in 2-propanol and PPTS, forming 38 in modest yield.
  • 89
    • 85088722537 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 91
    • 2142679778 scopus 로고
    • PhD Thesis; Harvard University: USA
    • (b) Bender, S. L. PhD Thesis; Harvard University: USA, 1986.
    • (1986)
    • Bender, S.L.1


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