Synthesis and structure of tolyporphin A O,O-diacetate

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1129-1132

  Wang, Wengui ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN; TOLYPORPHIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY DIFFRACTION;

MOLECULAR STRUCTURE; PORPHYRINS; SPECTRUM ANALYSIS; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 0033533635     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9902374     Document Type: Article

References (16)

1. For recent reviews on MDR, see: (a) Pastan, I.; Gottesman, M. M. Annu. Rev. Biochem. 1993, 62, 385.
2. (b) Simon, S. M.; Schindler, M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3497.
3. (a) Prinsep, M. R.; Caplan, F. R.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Am. Chem. Soc. 1992, 114, 385.
4. (b) Prinsep, M. R.; Patterson, G. M. L.; Larsen, L. K.; Smith, C. D. Tetrahedron 1995, 51, 10523.
5. (c) Prinsep, M. R.; Patterson, G. M. L.; Larsen, L. K.; Smith, C. D. J. Nat. Prod. 1998, 61, 1133.
6. (d) Morliere, P.; Maziere, J.-C.; Santus, R.; Smith, C. D.; Prinsep, M. R.; Stobbe, C. C.; Fenning, M. C.; Golberg, J. L.; Chapman, J. D. Cancer Res. 1998, 58, 3571.
7. Minehan, T. G.; Kishi, Y. Angew. Chem. Int. Ed. 1999, 38, 923.
8. Minehan, T. G.; Cook-Blumberg, L.; Kishi, Y.; Prinsep, M. R.; Moore, R. E. Angew. Chem. Int. Ed. 1999, 38, 926.
9. The numbering used in ref 2a is adopted in this paper.
10. Minehan, T. G.; Kishi, Y. Tetrahedron Lett 1997, 38. 6811.
11. Minehan, T. G.; Kishi, Y. Tetrahedron Lett. 1997, 38. 6815.
12. 4 at 0°C was used for this C-glycosidation. The 60% yield of 11 was based on the methyl α-glycoside used.
13. (S)-Silyl ketene acetal was prepared from L-(S)-glutamic acid in five steps by using the known procedure for the (R)-series, see: Ravid, U.; Silverstein, R. M.; Smith, L. R. Tetrahedron 1978, 34, 1449 and ref 3.
14. The product at this stage was a mixture of diastereomers due to the chiral centers at C.3, C.6, C.12, and/or C.16.
15. TLC analysis showed that the oxidation was very clean but the isolated yield was only around 30%.
16. We gratefully thank Dr. Michèle Prinsep for kindly providing a sample of natural tolyporphin A. Acetylation of tolyporphin A is known to form tolyporphin A O,O-diacetate (2b).