Total synthesis and absolute stereochemistry of (9R,10S)-epoxyheptadecan-4, 6-diyn-3-one, a diacylglycerol acyltransferase inhibitor from Panax ginseng

Tetrahedron Letters

Volumn 45, Issue 38, 2004, Pages 7077-7079

  Oh, Jung Hoon ^a   Lee, Hyun Sun ^a   Rho, Mun Chual ^a   Kim, Young Kook ^a   Lee, Hyeong Kyu ^a   Lee, Woo Song ^a   Kim, Jae Nyoung ^b   Lee, Sangku ^a   Jung, Sang Hun ^c  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Chonnam National University   (South Korea)

^c Chungnam National University   (South Korea)

Author keywords

Absolute configuration; Asymmetric synthesis; Epoxidation; Stereochemistry; Total synthesis

Indexed keywords

ACYLTRANSFERASE INHIBITOR; DIACYLGLYCEROL ACYLTRANSFERASE; EPOXYHEPTADECAN 4,6 DIYN 3 ONE; GINSENG EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; GINSENG; STEREOCHEMISTRY; STEREOISOMERISM;

PANAX; PANAX GINSENG;

EID: 4444363311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.153     Document Type: Article

References (9)

1. R.V. Farese Jr., S. Cases, and S.J. Smith Curr. Opin. Lipidol. 11 2000 229 234
2. R. Lejner, and A. Kuksis Prog. Lipid. Res. 35 1996 169 201
3. S.W. Lee, K. Kim, M.-C. Rho, M.Y. Chung, Y.H. Kim, S. Lee, H.S. Lee, and Y.K. Kim Planta Med. 70 2004 197 200
4. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765 5780
5. A.V.R. Rao, E.R. Reddy, A.V. Purandare, and Ch.V.N.S. Varaprasad Tetrahedron 43 1987 4385 4394
6. J.A. Marshall, and X.-j. Wang J. Org. Chem. 56 1991 960 969
7. 1H NMR analysis of the derived α-methoxy-α-(trifluoromethyl)phenylacetyl (MTPA, Mosher) ester, and >99% indicates that the other enantiomer was not detectable by NMR
8. 3) for (9S,10R)-2
9. 3) for (9S,10S)-4