Total synthesis of (+)-amphidinolide A. Structure elucidation and completion of the synthesis

Journal of the American Chemical Society

Volumn 127, Issue 39, 2005, Pages 13598-13610

  Trost, Barry M ^a   Harrington, Paul E ^a   Chisholm, John D ^a   Wrobleski, Stephen T ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; CYTOLOGY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; RUTHENIUM COMPOUNDS; STEREOCHEMISTRY; TOXICITY;

AMPHIDINOLIDE; CYTOTOXIC MACROLIDES; DIASTEREOMERS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALKENE; ALKYNE; AMPHIDINOLIDE A; RUTHENIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CYCLIZATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; ISOMERIZATION; LACTONIZATION; MACROLACTONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILYLATION; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

LACTONES; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE;

EID: 25844457422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053365y     Document Type: Article

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21. The location of the acetonide in 43 was not determined and is depicted arbitrarily for 43.
22. The relative stereochemistry was not determined.
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24. See the Supporting Information for a complete comparison of the spectroscopic data.