Stereoselective synthesis of the C1-C20 segment of the microsclerodermins A and B

Tetrahedron Letters

Volumn 47, Issue 40, 2006, Pages 7255-7258

  Chandrasekhar, S ^a   Sultana, S Shameem ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Deoxygenative rearrangement; Iterative Sharpless asymmetric dihydroxylation; Stereoselective

Indexed keywords

ANTIFUNGAL AGENT; CITRONELLOL; MICROSCLERODERMIN A; MICROSCLERODERMIN B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIHYDROXYLATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 33747889640     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.107     Document Type: Article

References (20)

1. Bewley C., Debitus C., and Faulkner D.J. J. Am. Chem. Soc. 116 (1994) 7631-7636
2. Qureshi A., Colin P.L., and Fulkner D.J. Tetrahedron 56 (2000) 3679-3685
3. Sasaki S., Hamada Y., and Shioiri T. Tetrahedron Lett. 38 (1997) 3013-3016
4. Sasaki S., Hamada Y., and Shioiri T. Tetrahedron Lett. 40 (1999) 3187
5. Sasaki S., Hamada Y., and Shioiri T. Synlett 4 (1999) 453-455
6. Chandrasekhar S., and Reddy M.V. Tetrahedron 56 (2000) 1111-1114
7. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019-8022
8. Guo C., and Lu X. J. Chem. Soc.,Chem. Commun. (1993) 394-395
9. Xu D., Crispino G., and Sharpless K.B. J. Am. Chem. Soc. 114 (1992) 7570-7571
10. Li G., Chang H.T., and Sharpless K.B. Angew. Chem., Int. Ed. 35 (1996) 451-455
11. For a review on asymmetric aminohydroxylation, see:. Bodkin J.A., and McLeod M.D. J. Chem. Soc., Perkin Trans. 1 (2002) 2733-2746
12. Gao D., and O'Doherty G.A. Org. Lett. 6 (2005) 1069-1072
13. The introduction of the azide functionality at C-3 was planned by another asymmetric dihydroxylation-double inversion (at C-3) sequence. Unfortunately, this method resulted in the elimination product 15b.{A figure is presented}
14. Ward R.S., Pelter A., Goubet D., and Pritchard M.C. Tetrahedron: Asymmetry 6 (1995) 469-498
15. Bernsmann H., Wang Y., Frohlich R., and Metz P. Tetrahedron 58 (2002) 4451-4457
16. Raghavan S., and Rasheed M.A. Tetrahedron: Asymmetry 14 (2003) 1371-1374
17. Scriven E., and Turnbull K. Chem. Rev. 88 (1988) 297-368
18. Yu J., Gaunt M.J., and Spencer J.B. J. Org. Chem. 67 (2002) 4627-4629
19. Rijsbergen R.V., Anteunis R.M.J.O., and Bruyn A.D. J. Carbohydr. Chem. 2 (1983) 395
20. ++1), found: 552.2722.