Regio- and stereoselective ring opening of epoxide with cyanoguanidine dianions, a facile synthesis of the K(atp) opener BMS-180448

Tetrahedron Asymmetry

Volumn 9, Issue 8, 1998, Pages 1337-1340

  Chen, Bang Chi ^a,b   Quinlan, Sandra L ^a   Reid, J Gregory ^a   Jass, Paul A ^b   Robinson, Tonya P ^b   Early, William A ^b   Delaney, Edward J ^b   Humora, Michael J ^b   Madding, Gary D ^b   Venit, John J ^b   Winter, William J ^b  

^a BRISTOL MYERS SQUIBB COMPANY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; DICYANODIAMIDE DERIVATIVE; EPOXIDE; GUANIDINE DERIVATIVE; N (4 CHLOROPHENYL) N' CYANO N'' (6 CYANO 3,4 DIHYDRO 3 HYDROXY 2,2 DIMETHYL 2H 1 BENZOPYRAN 4 YL)GUANIDINE; POTASSIUM CHANNEL; POTASSIUM CHANNEL STIMULATING AGENT; POTASSIUM ION; UNCLASSIFIED DRUG;

ARTICLE; DRUG SELECTIVITY; DRUG SYNTHESIS; ISCHEMIA; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032562588     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00116-5     Document Type: Article

References (20)

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16. 12. The epoxide (3S,4S)-12 can be prepared enantiomerically via Jacobsen's epoxidation, see: Lee, N. H.; Muci, A. R.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 5055; or via microbial epoxidation, see: Woroniecki, S. R.; Sime, J. T.; Baggaley, K. H.; Elson, S. W. Biocatalysis 1993, 7, 221.
17. 12. The epoxide (3S,4S)-12 can be prepared enantiomerically via Jacobsen's epoxidation, see: Lee, N. H.; Muci, A. R.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 5055; or via microbial epoxidation, see: Woroniecki, S. R.; Sime, J. T.; Baggaley, K. H.; Elson, S. W. Biocatalysis 1993, 7, 221.
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20. 14. For leading references on carbon-heteroatom bond formation using dianion chemistry, see Davis, F. A.; Reddy, R. T.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387; Davis, F. A.; Reddy, R. E. Tetrahedron: Asymmetry 1994, 5, 955.