An enantiospecific route to (+)-(1R,3S)-cis-chrysanthemic acid from (-)-d-pantolactone

Synthesis

Volumn , Issue 7, 2011, Pages 1067-1070

  Hajare, Atul K ^a,b   Datrange, Laxmikant S ^a   Murthy, Y L N ^b   Bhuniya, Debnath ^a   Reddy, D Srinivasa ^a,c  

^a Advinus Therapeutics Private Limited Bangalore   (India)

^b ANDHRA UNIVERSITY   (India)

^c NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

alkenes; metathesis; ring closure; stereoselective synthesis; Wittig reaction

Indexed keywords

ALKENES; METATHESIS; RING CLOSURES; STEREOSELECTIVE SYNTHESIS; WITTIG REACTION;

OLEFINS; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

2,2 DIMETHYL 3 (2 METHYLPROP 1 ENYL)CYCLOPROPANECARBOXYLIC ACID; 3,3,6,6 TETRAMETHYL 4 OXOBICYCLO[3.1.0]HEXAN 2 YL 4 TOLUENESULFONATE; 4 (METHOXYMETHOXY) 5,5 DIMETHYLCYCLOPENT 2 ENONE; 5 (METHOXYMETHOXY) 4,4 DIMETHYLHEPTA 1,6 DIEN 3 OL; 5,5 DIMETHYL 4 OXOCYCLOPENT 2 ENYL 4 TOLUENESULFONATE; CHRYSANTHEMIC ACID; PANTOLACTONE; PYRETHROID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOPROPANATION; ENANTIOSELECTIVITY; FRAGMENTATION REACTION; IONIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROPHOTOMETRY; SYNTHESIS;

EID: 79953029994     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258451     Document Type: Article

References (26)

1. Itagaki M, Suenobu K, Org. Process Res. Dev. 2007 11 509
2. Jeanmart S, Aust. J. Chem. 2003 56 559
3. Fishman A, Kellner D, Ioffe D, Shapiro E, Org. Process Res. Dev. 2000 4 77
4. Naumann K, Chemistry of Plant Protection, Synthetic Pyrethroid Insecticides Vol. 5 Springer Berlin 1990 and references cited therein
5. Selected references for previous syntheses:, Krief A, Jeanmart S, Kremer A, J. Org. Chem. 2008 73 9795
6. Krief A, Gondal H Y., Kremer A, Chem. Commun. 2008 4753
7. Krief A, Kremer A, Synlett 2007 607
8. Krief A, Swinnen D, Tetrahedron Lett. 1996 37 7123
9. Krief A, Surleraux D, Ropson N, Tetrahedron: Asymmetry 1993 4 289
10. Lambs L, Singh N P., Biellmann J F., J. Org. Chem. 1992 57 6301
11. Krief A, Surleraux D, Robson M J., Synlett 1991 276
12. Krief A, Surleraux D, Frauenrath H, Tetrahedron Lett. 1988 29 6157
13. Mulhr J, Kappert M, Angew. Chem., Int. Ed. Engl. 1983 22 63
14. Sobti R, Dev S, Tetrahedron 1974 30 2927
15. Krief A, Kremer A, Tetrahedron Lett. 2010 51 304
16. See earlier references from this group which use the pantolactone chiral pool approach:, Hajare A, Datrange L, Vyas S, Bhuniya D, Reddy D S., Tetrahedron Lett. 2010 51 5291
17. Reddy D S., Srinivas G, Rajesh B M., Kannan M, Rajale T V., Iqbal J, Tetrahedron Lett. 2006 47 6373
18. Hajare A, Ravikumar V, Khaleel S, Bhuniya D, Reddy D S., J. Org. Chem. 2011 76 963
19. Tombo G M. R., Bellus D, Angew. Chem., Int. Ed. Engl. 1991 30 1193
20. Elliott M, Pestic. Sci. 1989 27 337
21. Ackermann P, Bourgeois F, Drabek J, Pestic. Sci. 1980 11 169
22. Akbutina F A., Sandretdinov I F., Selezneva N K., Miftakhov M S., Mendeleev Commun. 2003 3 151
23. Pirrung F O. H., Hiemstra H, Speckamp W N., Kaptein B, Schoemaker H E., Synthesis 1995 458
24. Previously, the same alcohol was prepared from (-)-panto-lactone in 10 steps with an overall yield of 34% using an alternate route., Miyaoka H, Sagawa S, Nagaoka H, Yamada Y, Tetrahedron: Asymmetry 1995 6 587
25. Isopropyldiphenylsulfonium tetrafluoroborate was synthesized according to the general procedure reported in the literature:, Matsuyama H, Nakamura T, Iyoda M, J. Org. Chem. 2000 65 4796
26. Dauvergne J, Happe A M., Jadhav V, Justice D, Matos M.-C, McCormack P J., Pitts M R., Roberts S M., Singh S K., Snape T J., Whittall J, Tetrahedron 2004 60 2559