Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: Proof of concept

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2181-2184

  Lee, Jinhwa ^a   Kobayashi, Yoshihisa ^a   Tezuka, Kenichi ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC HYDROCARBON; ANTIINFECTIVE AGENT; MACROLIDE; OASOMYCIN;

ARTICLE; CHEMISTRY; CONFORMATION; FACTUAL DATABASE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ANTI-BACTERIAL AGENTS; DATABASES, FACTUAL; HYDROCARBONS, ACYCLIC; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0033619850     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990379y     Document Type: Article

References (10)

1. Kobayashi, Y.; Lee. J.; Tezuka, K.; Kishi, Y. Org. Lett. 1999, 1, 2177-2180.
2. Grabley, S.; Kretzschmar, G.; Mayer, M.; Philipps, S.; Thiericke, R.; Wink, J.; Zeeck, A. Liebigs Ann. Chem. 1993, 573-579.
3. CS ChemNMR Pro version 1.0. Renate Buergin Schaller, Development Centre, Bergstr. 114, Zurich. Switzerland, installed in CS ChemDraw Pro version 4.5, was used.
4. 2
5. The stereochemistry of 1a-h corresponds to that in the preceding paper.
6. The structure of the synthetic tetraol 6 was established by adopting the same procedure as the one described in the preceding paper. The experimental details are included in the Supporting Information.
7. 4/ MeOH/0°C.
8. We thank Dr. Gerhard Kretzschmar for a sample of oasomycins A, B, and C.
9. D value of synthetic tetraol 6 was found approximately +5.9° (c 1.2, MeOH). We were concerned that this value might be too small to draw our conclusion.
10. 2/rt.