Enantioselective synthesis of schulzeines B and C via a β-lactone-derived surrogate for bishomoserine aldehyde

Organic Letters

Volumn 11, Issue 5, 2009, Pages 1143-1146

  Liu, Gang ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALPHA GLUCOSIDASE; BIOLOGICAL PRODUCT; FUSED HETEROCYCLIC RINGS; LACTAM; LACTONE; SCHULZEINE B; SCHULZEINE C;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALPHA-GLUCOSIDASES; BIOLOGICAL PRODUCTS; HETEROCYCLIC COMPOUNDS, 3-RING; LACTAMS; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 64349084679     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802992m     Document Type: Article

References (21)

1. Takada, K.; Uehara, T.; Nakao, Y.; Matsunaga, S.; Van Soest, R. W. M.; Fusetani, N. J. Am. Chem. Soc. 2004, 126, 187.
2. (a) Kuntiyong, P.; Akkarasamiyo, S.; Eksinitkun, G. Chem. Lett. 2006, 35, 1008.
3. (b) Gurjar, M. K.; Pramanik, C.; Bhattasali, D.; Ramana, C. V.; Mohapatra, D. K. J. Org. Chem. 2007, 72, 6591.
4. (c) Wardrop, D. J.; Bowen, E. G. Abstracts of Papers, 233rd ACS National Meeting, Chicago, March 25-29, 2007.
5. For a review of glycosidase inhibitors, see: Jung, M.; Park, M.; Lee, H. C.; Kang, Y.-H.; Kang, E. S.; Kim, S. K. Curr. Med. Chem. 2006, 13, 1203.
6. This δ-lactone available from Aldrich ($104/25 g, 99% ee, 2008) is prepared by the method of Wynberg. See:
7. (a) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. For preparation using in situ ketene generation, see:
8. (b) Tennyson, R.; Romo, D. J. Org. Chem. 2000, 65, 7248.
9. Tennyson, R.; Cortez, G. C.; Galicia, H. J.; Kreiman, C. R.; Thompson, C. M.; Romo, D. Org. Lett. 2002, 4, 533.
10. (a) Jocic, Z. Z Zh. Russ. Fiz. Khim. Ova. 1897, 29, 97.
11. (b) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906 For mechanistic studies of the Jocic reaction, see:
12. (c) Reeve, W.; Wood, C. W. Can. J. Chem. 1980, 58, 485 For recent applications of Jocic-type reactions, see:
13. (d) Shamshina, J. L.; Snowden, T. S. Org. Lett. 2006, 8, 5881.
14. tBu) which mainly led to recovered starting material.
15. Qian, L.; Sun, Z.; Deffo, T.; Mertes, K. B. Tetrahedron Lett. 1990, 31, 6469.
16. The addition of 1 equiv of sulfuric acid to the LiAlH4 reduction led to greatly improved yields versus LiAlH4. See: Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464.
17. See Supporting Information for details.
18. (a) Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
19. (b) Taber, D. F.; Silverberg, L. J. Tetrahedron Lett. 1991, 32, 4227.
20. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
21. For a lead reference to sulfation methods, see: Simpson, L. S.; Widlanski, T. S. J. Am. Chem. Soc. 2006, 128, 1605.