The total synthesis of spirotryprostatin A

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1138-1140

  Edmondson, Scott D ^a   Danishefsky, Samuel J ^a,b  

^a Havemeyer Hall ^*  (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

2 oxindoles; Diketopiperazines; Spiro compounds; Spirotryprostatin A; Total synthesis

Indexed keywords

EID: 0032482105     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1138::AID-ANIE1138>3.0.CO;2-N     Document Type: Article

References (22)

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13. For a lead reference on the Pictet-Spengler reaction for the synthesis of cis-and trans-tetrahydrocarbolines, see: a) E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennett, J. M. Cook, W. H. Watson, M. Krawlec J. Org. Chem. 1997, 62, 44; b) E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797.
14. For a lead reference on the Pictet-Spengler reaction for the synthesis of cis-and trans-tetrahydrocarbolines, see: a) E. D. Cox, L. K. Hamaker, J. Li, P. Yu, K. M. Czerwinski, L. Deng, D. W. Bennett, J. M. Cook, W. H. Watson, M. Krawlec J. Org. Chem. 1997, 62, 44; b) E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797.
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17. 1H NMR spectra of 12: irradiated signal (enhancements), H4 (H8β, H19), H8α (H8β, H9, H18), H8β (H4, H8α, H19), H9 (H8α, H8β, H18), H18 (H8α, H9), H19 (H4, H5, H18).
18. 3): δ = 180.8, 174.4, 159.9, 141.2, 137.6 (2C), 131.7, 128.7, 128.3 (2C), 125.1, 124.2, 107.4, 97.2, 66.2, 59.1, 58.6, 55.5, 52.3, 48.0, 43.3, 41.3, 29.2, 29.1.
19. Yields based on recovered starting material. Actual yields are 57% for 9 and 31% for 11.
20. S. A. Boyd, W. J. Thompson J. Org. Chem. 1987, 52, 1790.
21. 3): δ = 181.7, 167.5, 166.8, 160.4, 142.4, 138.1 (2C), 131.7, 128.7, 128.5 (2C), 126.5, 119.2, 106.6, 97.6, 61.3, 58.7, 58.0, 55.4, 55.1, 48.3, 45.0, 42.8, 34.5, 27.9, 27.7, 26.5, 23.6.
22. For an example of racemization of phenylalanine derivatives under these conditions, see: R. D. Larsen, R. A. Reamer, E. G. Corely, P. Davis, E. J. J. Grabowski, P. J. Reider, I. Shinkai J. Org. Chem. 1991, 56, 6034.