Saframycin analog

Figure 15.11 Enantioselective solid-phase synthesis of saframycin analogs by the Myers group [36, 39, 40],...

The desired Saframycin analog was thus prepared in an extraordinary 53% overall yield for a ten-step sequence. Besides the compound shown, 22 additional analogs were prepared, 16 of them by simultaneous parallel synthesis. 

Liu, Z., Wang, Y., Tang, Y, Chen, S Chen, X., and Li, H. (2006) Synthesis and antitumor activity of simplified ecteinascidin-saframycin analogs. Bioorg. Med. Chem. Lett., 16, 1282-1285. 

Myers and Lanman [405] have reported the preparation of stractural analogs of Saframycin on a soHd support (Scheme 120). 

FIGURE 11.66 Saframycin A structure and 3,9-diazabicyclo[3.3.1]non-6-ene core. (From Myers, A.G. and Lanman, B.A., A solid-supported, enantioselective synthesis suitable for the rapid preparation of large numbers of diverse stractural analogs of (-)-saframycin A, 7. Am. Chem. Soc., 124, 12969, 2002 Orain, D., Koch, G., and Giger, R., From solution phase studies to solid-phase synthesis a new indole based scaffold for combinatorial chemistry, Chimia, 57, 255, 2003.)... 

Myers, A.G. and Lanman, B.A., A solid-supported, enantioselective synthesis suitable for the rapid preparation of large numbers of diverse structural analogs of (-)-saframycin A, J. Am. Chem. Soc., 124, 12969, 2002. 

Scheme 11 Total Synthesis of Saframycin A analogs on solid phase by Myers et al.

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