Two Complimentary Methods for the Synthesis of the Terminal N-Alkenyl-N-methylformamide Group Found in Cytotoxic Marine Macrolides

Synlett

Volumn 1996, Issue 3, 1996, Pages 209-211

  Paterson, Ian ^a   Cowden, Cameron ^a   Watson, Christine ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000295111     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5383     Document Type: Article

References (28)

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16. For previous work, see: (a) Paterson, I.; Yeung, K.-S. Tetrahedron Lett. 1993, 34, 5347. (b) Paterson, I.; Smith, J. D. Tetrahedron Lett. 1993, 34, 5351. Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405.
17. For previous work, see: (a) Paterson, I.; Yeung, K.-S. Tetrahedron Lett. 1993, 34, 5347. (b) Paterson, I.; Smith, J. D. Tetrahedron Lett. 1993, 34, 5351. Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405.
18. In their recent synthesis of aplyronine A (ref 3b) and aplyronines B and C (ref 3c), Yamada et al. incorporated the N-alkenyl-N-methylformamide terminus by acid-catalysed (PPTS, hydroquinone) condensation of N-methylformamide with an aldehyde. Pattenden et al. have also reported a synthesis of an ulapualide segment containing an N-alkenyl-N-methylformamide group, although the conditions and yield for the incorporation of the latter were not disclosed. Kiefel, M. J.; Maddock, J.; Pattenden, G. Tetrahedron Lett. 1992, 33, 3227.
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20. All new compounds gave spectroscopic data in agreement with the assigned structures. Aldehydes 9 and 22 were prepared from the previously described alkene i, while 8 was prepared from the ketophosphonate ii (ref 9a). (Matrix Presented)
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22. For some examples, see: (a) Martin, S. F.; Chou, T.-S.; Payne, C. W. J. Org. Chem. 1977, 42, 2520. (b) Seemuth, P. D.; Zimmer, H. J. Org. Chem. 1978, 43, 3063. Broekhof, N. L. J. M.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1980, 21, 2671. Heymes, A; Chekroun, I. Synthesis 1987, 245.
23. For some examples, see: (a) Martin, S. F.; Chou, T.-S.; Payne, C. W. J. Org. Chem. 1977, 42, 2520. (b) Seemuth, P. D.; Zimmer, H. J. Org. Chem. 1978, 43, 3063. Broekhof, N. L. J. M.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1980, 21, 2671. Heymes, A; Chekroun, I. Synthesis 1987, 245.
24. For some examples, see: (a) Martin, S. F.; Chou, T.-S.; Payne, C. W. J. Org. Chem. 1977, 42, 2520. (b) Seemuth, P. D.; Zimmer, H. J. Org. Chem. 1978, 43, 3063. Broekhof, N. L. J. M.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1980, 21, 2671. Heymes, A; Chekroun, I. Synthesis 1987, 245.
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27. For reviews of the Wittig reaction, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. (b) Vedejs, E.; Peterson, M. J. In Topics in Stereochemistry, Vol 21, p 1, Eliel, E. L.; Wilen, S. H., Eds., Wiley; New York (1994).
28. 3 requires 306.2069.