Anodic Cyclization Reactions: Reversing the Polarity of Ketene Dithioacetal Groups

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1729-1732

  Sun, Yongmao ^a   Liu, Bin ^a   Kao, Jeff ^a   Andre' D'Avignon, D ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; KETONE; THIOACETAMIDE;

ARTICLE; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; KETONES; OXIDATION-REDUCTION; STEREOISOMERISM; THIOACETAMIDE;

EID: 0035979050     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015925d     Document Type: Article

References (26)

1. For a review of synthetic applications of anodic electrochemistry, see: Moeller, K. D. Tetrahedron 2000, 56, 9527.
2. For selected examples, see: (a) Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372.
3. (b) Frey, D. A.; Reddy, S. H. K.; Moeller, K. D. J. Org. Chem. 1999, 64, 2805.
4. (c) Moeller, K. D.; Tinao, L. V. J. Am. Chem. Soc. 1992, 114, 1033.
5. New, D. G.; Tesfai, Z.; Moeller, K. D. J. Org. Chem. 1996, 61, 1578.
6. Silyl-substituted enol ethers have been used in anodic coupling reactions. For a single example using an oxygen nucleophile, see: (a) Sutterer, A.; Moeller, K. D. J. Am. Chem. Soc. 2000, 122, 5636. For three examples leading to carbon-carbon bond formation, see:
7. (b) Reddy, S. H. K.; Chiha, K.; Sun, Y.; Moeller, K. D. Tetrahedron. In press.
8. A pair of cyclization reactions resulting from the intramolecular coupling of a ketene dithioacetal group with a trisubstituted olefin using eerie ammonium nitrate and a related coupling using a styrene terminating group have been reported: Snider, B. B.; Shi, B.; Quickley, C. A. Tetrahedron 2000, 56, 10127.
9. For a single example of a cyclic ketene acetal being coupled to an allylsilane terminating group with the use of a vanadium(V) ester, see: Ryter, K.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 2658.
10. For previous syntheses of scopadulcic acid B, see: (a) Ziegler, F. E.; Wallace, O. B. J. Org. Chem. 1995, 60, 3626.
11. (b) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042. For other related synthetic efforts, see:
12. (c) Robichaud, A. J.; Meyers, A. I. J. Org. Chem. 1991, 56, 2607.
13. (d) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328.
14. (e) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304.
15. For a review on the use of ketene dithioacetals in synthesis, see: Kolb, M. Synthesis 1990, 171.
16. (a) For the conversion of esters to ketene dithioacetals, see: Corey, E. J.; Kozikowski, A. P. Tetrahedron Lett. 1975, 16, 925.
17. (b) Substrates 4a and 4b were made from the commercially available alcohol esters.
18. (a) The oxidations were conducted using a Model 630 coulometer, a Model 410 potentiostatic controller, and a Model 420A power supply purchased from The Electrosynthesis Co., Inc.
19. (b) For a simple setup to try electrochemical reactions using a battery as a power supply, see: Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996, 37, 8317.
20. 3a
21. For asymmetric syntheses of (+)-nemorensic acid, see: (a) Honda, T.; Ishikawa, F. J. Org. Chem. 1999, 64, 5542.
22. (b) Dillon, M. P.; Lee, N. C.; Stappenbeck, F.; White, J. D. J. Chem. Soc. Chem. Commun. 1995, 1645. For a racemic synthesis of nemorensic acid, see:
23. (c) Klein, L. L. J. Am. Chem. Soc. 1985, 107, 2573.
24. (a) Chamberlin, A. R.; Nguyen, G. D.; Chung, J. Y. L. J. Org. Chem. 1984, 49, 1682.
25. (b) Corey, E. J.; Beames, J. D. J. Am. Chem. Soc. 1973, 95, 5829.
26. For a comparison of enol ether and allylsilane trapping groups, see: Tinao-Wooldridge, L. V.; Moeller, K. D.; Hudson, C. M. J. Org. Chem. 1994, 59, 2381 along with ref 3b. For a comparison of allylsilane and alcohol trapping groups, see ref 3a.