The synthesis of the monomeric moiety of disorazole C1

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2821-2824

  Hillier, M C ^a   Park, D H ^a   Price, A T ^a   Ng, R ^a   Meyers, A I ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; DISORAZOLE C1; MACROLIDE; MONOMER; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034656194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00271-9     Document Type: Article

References (23)

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3. For a general review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 50, Chapter 1.
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12. 19F NMR
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20. We found that conversion of the iodide 20 to the vinyl tin species, followed by removal of the p-methoxybenzyl group with DDQ resulted in destannylation, thus providing 21
21. 2 in this reaction did not provide product.
22. The Stille coupling also resulted in the formation of a small of amount (<5%) of the homocoupled byproduct 22
23. Unfortunately, the monomer 2 is somewhat unstable and slowly isomerizes even when stored at -20°C.