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Volumn 65, Issue 6, 2000, Pages 1738-1742

Formal total synthesis of (-)-balanoh: Concise approach to the hexahydroazepine segment based on RCM

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BALANOL; HEXAMETHYLENEIMINE DERIVATIVE; METHANOL DERIVATIVE; MOLYBDENUM COMPLEX; RUTHENIUM COMPLEX;

EID: 0038644039     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991611g     Document Type: Article
Times cited : (141)

References (59)
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    • For the preparation and biological evaluation of balanol analogues see the following for leading references: (a) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215. (c) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226. (d) Mendoza, J. S.; Jagdmann, G. E.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211 and references therein.
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    • For the preparation and biological evaluation of balanol analogues see the following for leading references: (a) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215. (c) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226. (d) Mendoza, J. S.; Jagdmann, G. E.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211 and references therein.
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    • and references therein
    • For the preparation and biological evaluation of balanol analogues see the following for leading references: (a) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215. (c) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226. (d) Mendoza, J. S.; Jagdmann, G. E.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211 and references therein.
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    • For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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    • For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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    • For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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    • For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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    • For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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    • note
    • (a) The synthesis described by Naito et al. requires nine steps and includes the resolution of racemic 3 as the final steps, cf. ref 7. (b) Very recently, an RCM-based approach to 3 has been reported that is distictly different from our one; it makes use of D-serine as the starting material and comprises a 14-step linear sequence, cf. ref 12a.
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    • For a short account see: Fürstner, A. Synlett 1999, 1523.
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    • For some total syntheses from our laboratory that we consider to adhere to these objectives see: (a) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9130
    • Fürstner, A.1    Langemann, K.2
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    • Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37. (e) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Methathesis Polymerization, 2nd ed.; Academic Press: New York, 1997.
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    • Grubbs, R.H.1    Chang, S.2
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    • (1997) Top. Catal. , vol.4 , pp. 285
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    • Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37. (e) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Methathesis Polymerization, 2nd ed.; Academic Press: New York, 1997.
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    • Schuster, M.1    Blechert, S.2
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    • Academic Press: New York
    • Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37. (e) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Methathesis Polymerization, 2nd ed.; Academic Press: New York, 1997.
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    • 3 as shown in Scheme 4. Originally, it was believed that the complex thus formed is a ruthenium allenylidene species: cf. Harlow, K. J.; Hill, A. F.; Winton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. More detailed study, however, has shown that it is the rearranged product, i.e., the indenylidene ruthenium complex 18: cf. Hill, A. F.; Fürstner, A.; Liebl, M.; Mynott, R.; Gabor, B.; Jafarpour, L.; Nolan, S. P., manuscript in preparation.
    • (1999) J. Chem. Soc., Dalton Trans. , pp. 285
    • Harlow, K.J.1    Hill, A.F.2    Winton-Ely, J.D.E.T.3
  • 50
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    • manuscript in preparation
    • 3 as shown in Scheme 4. Originally, it was believed that the complex thus formed is a ruthenium allenylidene species: cf. Harlow, K. J.; Hill, A. F.; Winton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. More detailed study, however, has shown that it is the rearranged product, i.e., the indenylidene ruthenium complex 18: cf. Hill, A. F.; Fürstner, A.; Liebl, M.; Mynott, R.; Gabor, B.; Jafarpour, L.; Nolan, S. P., manuscript in preparation.
    • Hill, A.F.1    Fürstner, A.2    Liebl, M.3    Mynott, R.4    Gabor, B.5    Jafarpour, L.6    Nolan, S.P.7
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    • (b) For a general review on Mitsunobu reactions see: Mitsunobu, O. Synthesis 1981, 1.
    • (1981) Synthesis , pp. 1
    • Mitsunobu, O.1


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