First construction of a saricandin analog corresponding to papulacandin D

Synthesis

Volumn , Issue 6, 2001, Pages 833-840

  Hamdouchi, Chafiq ^a   Sanchez Martinez, Concha ^b  

^a ELI LILLY AND COMPANY   (United States)

^b ELI LILLY AND COMPANY   (Spain)

Author keywords

Antifungal; Enatioselective reduction; Papulacandin; Saricandin

Indexed keywords

ASSAYS; CATALYSIS; ENZYMES; PALLADIUM; REDUCTION;

CHIRAL BUILDING BLOCKS;

SYNTHESIS (CHEMICAL);

AB 2202W 161; ANTIFUNGAL AGENT; GLYCOSIDE; PAPULACANDIN D; PAPULACANDIN DERIVATIVE; REAGENT; SARICANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CHEMICAL BINDING; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0035036555     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13399     Document Type: Article

References (24)

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22. For an excellent review, see: Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, P. S. Synthesis 1994, 639.
23. The reason of this selection is supported by the fact that Barrett's approach is the only known efficient approach that delivers directly the spiroketal nucleus bearing the protecting group of choice for the generation of the correct monoester. On the other hand their study on protecting groups demonstrated that the protecting group of choice for this type of systems are O-4",O-6"-di-tert-butylsilylene, and phenol tris(triisopropylsilyl) (formula presented)
24. 2 solvents turned out to be very useful and was applied successfully for the purification of other polar compounds from tetrabutylammonium salts and other salts that derived from Wittig or Horner-Emmons reactions.