Structure Elucidation of (+)-Amphidinolide A by Total Synthesis and NMR Chemical Shift Analysis

Journal of the American Chemical Society

Volumn 126, Issue 16, 2004, Pages 5028-5029

  Trost, Barry M ^a   Harrington, Paul E ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE A;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; ISOMER; MATERIAL STATE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ANIMALS; CATALYSIS; CYCLIZATION; DINOFLAGELLIDA; EPOXY COMPOUNDS; LACTONES; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 1942489377     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049292k     Document Type: Article

References (10)

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3. (a) Lam, H. W.; Pattenden, G. Angew. Chem., Int. Ed. 2002, 41, 508.
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5. (c) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. A.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420 and references therein.
6. The epoxide to tetraol correlation was determined sequentially by NOE between H11 and H13, H13 and H15, and H15 and H18.
7. Alcohol 12 was prepared in three steps from (-)-diethyl tartrate: Rzepecki, P. W.; Prestwich, G. D. J. Org. Chem. 2002, 67, 5454.
8. 3OD, protons 4, 6a, 6b, 12, and 28b deviated by 0.01 ppm.
9. Carbons 3-5, 9, 13, 22, 24, 25, and 27-29 deviated by 0.1 ppm.
10. Kita, Y.; Maeda, H.; Omori, K.; Okuno, T.; Tamura, Y. Synlett 1993, 273.