Discovery through total synthesis - Epimerization at C7 in the CP compounds: Is (7S)-CP-263,114 a fermentation product?

Angewandte Chemie - International Edition

Volumn 38, Issue 21, 1999, Pages 3197-3201

  Meng, Dongfang ^a,b   Tan, Qiang ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

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

Author keywords

Epimerization; Natural products; Polycycles

Indexed keywords

NATURAL PRODUCT; POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FERMENTATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033517815     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991102)38:21<3197::AID-ANIE3197>3.0.CO;2-6     Document Type: Article

References (40)

1. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
2. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
3. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
4. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
5. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
6. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
7. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
8. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
9. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
10. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
11. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
12. Representative synthetic approaches to 1 and 2: K. C. Nicolaou, M. W. Harter, L. Boulton, B. Jandeleit, Angew. Chem. 1997, 109, 1243; Angew. Chem. Int. Ed. Engl. 1997, 36, 1194; K. C. Nicolaou, M. H. D. Postema, N. D. Miller, G. Yang, Angew. Chem. 1997, 109, 2922; Angew. Chem. Int. Ed. Engl. 1997, 36, 2821; H. M. L. Davies, R. Calvo, G. Ahmed. Tetrahedron Lett. 1997, 38, 1737; P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157; A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552; N. Waizumi, T. Ito, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015; C. Chen. M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784; M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 890; K. C. Nicolaou, P. S. Baran, R. Jautelat, Y. He, K. C. Fong, H.-S. Choi, W. H. Yoon, Y.-L. Zhong. Angew. Chem. 1999, 111, 532; Angew. Chem. Int. Ed. 1999, 38, 549.
13. The first total syntheses of CP-225,917 and CP-263,114 were accomplished quite recently by Nicolaou and co-workers; a) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669; b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781; Angew. Chem. Int. Ed. 1999, 38, 1676.
14. The first total syntheses of CP-225,917 and CP-263,114 were accomplished quite recently by Nicolaou and co-workers; a) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669; b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781; Angew. Chem. Int. Ed. 1999, 38, 1676.
15. The first total syntheses of CP-225,917 and CP-263,114 were accomplished quite recently by Nicolaou and co-workers; a) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669; b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781; Angew. Chem. Int. Ed. 1999, 38, 1676.
16. The first total syntheses of CP-225,917 and CP-263,114 were accomplished quite recently by Nicolaou and co-workers; a) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669; b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781; Angew. Chem. Int. Ed. 1999, 38, 1676.
17. a) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky. Angew. Chem. 1998, 110, 1978; Angew. Chem. Int. Ed. 1998, 37, 1877;
18. a) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky. Angew. Chem. 1998, 110, 1978; Angew. Chem. Int. Ed. 1998, 37, 1877;
19. b) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky, Angew. Chem. 1998, 110, 1981;
20. Angew. Chem. Int. Ed. 1998, 37, 1880;
21. D. Meng, S. J. Danishefsky, Angew. Chem. 1999, 111, 1582; Angew. Chem. Int. Ed. 1999, 38, 1485.
22. D. Meng, S. J. Danishefsky, Angew. Chem. 1999, 111, 1582; Angew. Chem. Int. Ed. 1999, 38, 1485.
23. |3c| this center (C7) had been numbered as C12 before the full construction of the CP system had been completed. We now return to the numbering system proposed by Kaneko et al. [5,6]
24. T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594.
25. T. T. Dabrah, H. J. Harwood, Jr., L. H. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, J. Antibiot. 1997, 50, 1.
26. T. Okazoe, K. Takai, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 951.
27. 1H NMR spectra.
28. Recent examples of singlet-oxygen oxidation of furans can be found in dysidiolide syntheses: a) E. J. Corey, B. E. Roberts, J. Am. Chem. Soc. 1997, 119, 12425; b) S. R. Magnuson, L. Sepp-Lorenzino, N. Rosen, S. J. Danishefsky, J. Am. Chem. Soc. 1998, 120, 1615.
29. Recent examples of singlet-oxygen oxidation of furans can be found in dysidiolide syntheses: a) E. J. Corey, B. E. Roberts, J. Am. Chem. Soc. 1997, 119, 12425; b) S. R. Magnuson, L. Sepp-Lorenzino, N. Rosen, S. J. Danishefsky, J. Am. Chem. Soc. 1998, 120, 1615.
30. The authors thank Dr. T. Kaneko and Dr. T. T. Dabrah of the Pfizer Central Research for providing a trace sample of natural CP-225,917 and several small samples of CP-263,114 from separate fermentation processes.
31. Use of trimethylsilyldiazomethane leads to a trimethyl ester as the product from a ring opening of the anhydride. Some diazomethane methylations required 2-pentene as cosolvent to prevent side reactions at the two side-chain olefins.
32. +: 589.2413, found: 589.2391.
33. +: 589.2413, found: 589.2415.
34. The trace fermentation acid samples came from several different sources which differed in the amount of the 75 system 17 (and subsequently its methyl ester 11). The ratio of 2:17 did not change following storage of the samples in our premises for five months at -78°C.
35. 3CN. We note also that the chromatography per se does not effect the homogeneity of the samples. Hence, we are confident that the 7S isomer we detected was present in the original samples.
36. Dess-Martin periodinane: a) D. B. Dess. J. C. Martin, J. Org. Chem. 1983, 48, 4155; b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; c) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549; d) R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899; review of TPAP/ NMO oxidation: S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
37. Dess-Martin periodinane: a) D. B. Dess. J. C. Martin, J. Org. Chem. 1983, 48, 4155; b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; c) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549; d) R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899; review of TPAP/ NMO oxidation: S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
38. Dess-Martin periodinane: a) D. B. Dess. J. C. Martin, J. Org. Chem. 1983, 48, 4155; b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; c) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549; d) R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899; review of TPAP/ NMO oxidation: S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
39. Dess-Martin periodinane: a) D. B. Dess. J. C. Martin, J. Org. Chem. 1983, 48, 4155; b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; c) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549; d) R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899; review of TPAP/ NMO oxidation: S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
40. Dess-Martin periodinane: a) D. B. Dess. J. C. Martin, J. Org. Chem. 1983, 48, 4155; b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; c) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549; d) R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899; review of TPAP/ NMO oxidation: S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.