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Volumn 121, Issue 27, 1999, Pages 6355-6366

Total synthesis of motuporin (nodularin-v)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOGINOSIN; MOTUPORIN; NODULARIN; PHOSPHOPROTEIN PHOSPHATASE 1; PHOSPHOPROTEIN PHOSPHATASE 2A; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0033554026     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9811243     Document Type: Article
Times cited : (73)

References (48)
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    • Total synthesis of calyculin C: (a) Scarlato, G. R.; Demattei J. A.; Chong L. S.; Ogawa A. K.; Lin, M. R.; Armstrong R. W. J Org. Chem. 1996, 61, 6139-6152. (b) Ogawa A. K.; DeMattei, J. A.; Scarlato, G. R.; Tellew, J. E.; Chong, L. S.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6153-6161. Ogawa, A. K.; Armstrong, R. W. J. Am. Chem. Soc. 1998, 120, 12435-12442. Synthetic efforts toward Tautomycin: Maurer K. W.; Armstrong R. W. J. Org. Chem. 1996, 61, 3106-3116. Biological activity and binding: (e) Gupta, V.; Ogawa, A. K.; Du, X. H.; Houk, K. N.; Armstrong, R. W. J. Med. Chem. 1997, 40, 3199-3206.
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    • Total synthesis of calyculin C: (a) Scarlato, G. R.; Demattei J. A.; Chong L. S.; Ogawa A. K.; Lin, M. R.; Armstrong R. W. J Org. Chem. 1996, 61, 6139-6152. (b) Ogawa A. K.; DeMattei, J. A.; Scarlato, G. R.; Tellew, J. E.; Chong, L. S.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6153-6161. Ogawa, A. K.; Armstrong, R. W. J. Am. Chem. Soc. 1998, 120, 12435-12442. Synthetic efforts toward Tautomycin: Maurer K. W.; Armstrong R. W. J. Org. Chem. 1996, 61, 3106-3116. Biological activity and binding: (e) Gupta, V.; Ogawa, A. K.; Du, X. H.; Houk, K. N.; Armstrong, R. W. J. Med. Chem. 1997, 40, 3199-3206.
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    • For other syntheses of ADDA see: (a) Namakoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349. (b) Chakraborty, T. K.; Joshi, T. P. Tetrahedron Lett. 1990, 31, 2043. (c) Beatty, M. F.; Jennings-White, C.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637. (d) Kim, H. Y.; Toogood, P. L. Tetrahedron Lett. 1996, 37, 2349-2352. (e) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1996, 37, 5645-5648. (f) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996 61, 4870. (g) D'Aniello, F.; Mann, A.; Schoenfelder, A.; Taddei, M. Tetrahedron 1997 53, 1447-1456. (h) Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4914-4915.
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    • note
    • Initial attempts with the chloride were successful; however, the reaction only progressed to ca. 50% completion. Given the potential for explosion afforded by the reaction conditions we were reluctant to continue the reaction for a longer duration.
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    • note
    • Prepared in two steps by protecting methyl lactate with benzyl bromide and sodium hydride in DMF followed by reducing the ester to the aldehyde with diisobutylaluminum hydride in toluene at -78 °C.
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    • note
    • The α-center of the threonyl residue was postulated as the site of epimerization as the diastereomers showed opposite but nearly equal optical rotations. This was in agreement with the optical rotations for the separate Ugi derived cyclohexenamide dipeptides 4(R) and 4(S) which were known to be epimers at this center and showed similar optical rotations. While the coupling gave a major and a minor component (presumably due to epimerization via the azalactone), the figures and Experimental Section show the manipulations of the minor diastereomer.
  • 48


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