Synthesis of 2-C-methylerythritols and 2-C-methylthreitols via enantiodivergent Sharpless dihydroxylation of trisubstituted olefins

Tetrahedron Letters

Volumn 53, Issue 22, 2012, Pages 2706-2708

  Ghosh, Shibaji K ^a   Butler, Mark S ^a,b   Lear, Martin J ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Antibiotic; Dudley; Enantiodivergent; Erythritol; Malaria; Mevalonate; Microbial; Parasitic; Sharpless; Tetraols; Threitol

Indexed keywords

2 METHYLERYTHREITOL; 2 METHYLTHREITOL; ALKENE DERIVATIVE; ERYTHRITOL; NATURAL PRODUCT; UNCLASSIFIED DRUG;

DIHYDROXYLATION; ENANTIOSELECTIVITY; REVIEW; STEREOISOMERISM; SYNTHESIS;

EID: 84860218200     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.03.071     Document Type: Article

References (22)

1. S.K. Ghosh, B. Somanadhan, K.S.-W. Tan, M.S. Butler, and M. Lear J. Org. Lett. 14 2012 1560 1563
2. J.H. Ch'ng, S.R. Kotturi, A.L. Chong, M.J. Lear, and K.W. Tan Cell Death Dis. 1 2010 e26
3. M.-H. Ngai, P. Yang, K. Liu, Y. Shen, M.R. Wenk, S.Q. Yao, and M.J. Lear Chem. Commun. 46 2010 8335 8337
4. A. Ali, M.R. Wenk, and M.J. Lear Tetrahedron Lett. 50 2009 5664 5666
5. H.-Y. Song, M.-H. Ngai, P.A. MacAry, J. Hobley, and M.J. Lear Org. Biomol. Chem. 7 2009 3400 3406
6. M. Rohmer Nat. Prod. Rep. 16 1999 565 574
7. W. Eisenreich, M. Schwarz, A. Cartayrade, D. Arigoni, M.H. Zenk, and A. Bacher Chem. Biol. 5 1998 R221 R233
8. N. Singh, G. Chevé, M.A. Avery, and C.R. McCurdy Curr. Pharm. Des. 13 2007 1161 1177
9. H. Jomar, J. Wisner, S. Sanderbrand, B. Altineicek, C. Weidemeyer, M. Hintz, I. Turbachova, M. Eberl, J. Zeidler, H.K. Lichtenthaler, D. Soldati, and E. Beck Science 285 1999 1573 1576
10. R. Ruangweerayut, S. Looareesuwan, D. Hutchinson, A. Chauemung, V. Banmairuroi, and K. Na-Bangchang Malar. J. 31 2008 225
11. M. Rohmer Prog. Drug Res. 50 1998 135 154
12. A. Fontana, R. Messina, A. Spinella, and G. Cimino Tetrahedron Lett. 41 2000 7559 7562
13. J.-L. Giner, W.V. Ferris, and J.J. Mullins J. Org. Chem. 67 2002 4856 4859
14. D. Enders, E. Peiffer, and G. Raabe Synthesis 2007 1021 1026
15. A.R. Moen, K. Ruud, and T. Anthonsen Eur. J. Org. Chem. 2007 1262 1266
16. M. Urbansky, C.E. Davis, J.D. Surjan, and R.M. Coates Org. Lett. 6 2004 135 138
17. E.J. Corey, G.-P. Angel, and M.C. Noe J. Am. Chem. Soc. 117 1995 10805 10816
18. E.O. Nwoye, and G.B. Dudley Chem. Commun. 2007 1436 1437
19. P. Dupau, R. Epple, A.A. Thomas, V.V. Fokin, and K.B. Sharpless Adv. Synth. Catal. 344 2002 421 433
20. C.W. Ford Phytochemistry 20 1981 2019 2020
21. K. Ogawa, and Y. Sashida Phytochemistry 31 1992 3657 3658
22. M. Ueda, Y. Sahtone, K. Ueda, and S. Yamamura Tetrahedron Lett. 42 2001 3109 3111