A novel face specific Mannich closure providing access to the saframycin-ecteinascidin series of piperazine based alkaloids

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2043-2046

  Zhou, Bishan ^a   Guo, Jinsong ^a   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; PIPERAZINE DERIVATIVE; SAFRAMYCIN; SAFRAMYCIN A; SAFRAMYCIN B; TRABECTEDIN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG CONFORMATION; DRUG STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034719740     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00106-4     Document Type: Article

References (12)

1. Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039.
2. (a) Arai, T.; Takahashi, K.; Kubo, A. J. Antibiot. 1977, 30, 1015.
3. (b) Arai, T.; Takahashi, K.; Ishiguro, K.; Mikami, T. Gann. 1980, 71, 790.
4. Sakai, R.; Rinehart, K. L.; Guan, Y.; Wang, A. Proc. Natl. Acad. Sci. USA 1992, 89, 11456.
5. Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
6. For recent reviews, see: (a) Pommier, Y.; Kohlhagen, G.; Bailly, C.; Waring, M.; Mazumder, A.; Kohn, K. Biochemistry 1996, 35, 13303.
7. For recent reviews, see: (a) Pommier, Y.; Kohlhagen, G.; Bailly, C.; Waring, M.; Mazumder, A.; Kohn, K. Biochemistry 1996, 35, 13303. (b) Martinez, E. J.; Owa, T.; Schreiber, S. L.; Corey, E. J. Proc. Natl. Acad. Sci. USA 1999, 96, 3496.
8. Danishefsky, S. J.; Harrison, P. J.; Webb, R. R.; O'Neill, B. T. J. Am. Chem. Soc. 1985, 107, 1421.
9. Cabre-Castellvi, J.; Polomo-Coll, A.; Palomo-Coll, A. C. Synthesis 1981, 616.
10. Attempts to reach 6 by means of a 3-point attachment of a formic acid equivalent were unsuccessful. Only with the aromatic aldehyde in place was cyclization realized.
11. The stereochemistry assigned to 6 and 11 was verified by a crystallographic determination at a later stage of the synthetic sequence.
12. Subsequent studies reveal that the stereochemical outcome of the Mannich closure step is also a function of the substitution pattern on the aldehyde-containing aromatic ring that enters into the cyclization event. These matters will be discussed in a fuller treatment of the subject.