The triumph of zinc: A short and highly efficient synthesis of the calyculin C1-C9 tetraene building block by Negishi coupling

Synlett

Volumn , Issue 12, 1999, Pages 1966-1968

  Pihko, Petri M ^a,c   Koskinen, Ari M P ^b,c  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b AALTO UNIVERSITY   (Finland)

^c UNIVERSITY OF OULU   (Finland)

Author keywords

Calyculins; Negishi coupling; Palladium catalyzed cross coupling; Polyenes; Stille coupling

Indexed keywords

CALYCULIN DERIVATIVE; CALYCULINAMIDE DERIVATIVE; CYTOTOXIC AGENT; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0032755184     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2979     Document Type: Article

References (28)

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23. Since an excess of the stannane 8 was used, the yield calculated based on the stannane was 66%. However, given the high efficiency of the reaction, such an excess is probably unnecessary.
24. 2Sn) 417.1815, found 417.1812, Δ = 0.7 ppm.
25. On a less than 1 mmol scale, the Michaelis-Becker reaction (step 2) often gives low yields due to lower concentrations and decomposition of the phosphite. We are currently optimizing the reaction conditions with different types of phosphites, with the ultimate aim of increasing the selectivity of the final projected Homer-Wadsworth-Emmons reaction. These studies will be reported elsewhere.
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