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Stereostructure of nystatin A1: A synthetic assignment of the C1–C10 fragment

✍ Scribed by Jacques Prandi; Jean-Marie Beau

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
289 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The 3R, SR and 7R cOnfigUrQtiOtI.3 for nystatin A hQV@ been aSSigned through a comparison of synthetic and natural fmgment 3. The key step sf {he synthetic sequence is a nucleophilic oxirane opening by an a-glycosyl copper reagent. We recently reported1 the 3R*, 5R* and 7R* relative configurations for nystatin Al, a commonly used antibiotic in human therapy*. The stereochemical information was deduced by detailled 6 $ M=Li J I1 X=OH, Y=H 13 X=OH 9' M=CH30C(CH3)2CrCCu 12 X=H, Y=OH e c 14 x=1 Li 0 h @c i -AcO ,,,,-OAc -17 3 g 15 X=CH2 c 16 X=0 Scheme:

(TBS = t-butyldimethylsilyl) (a) Bu2Sn0, NBuqBr,

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Synthesis and stereochemical assignment
Synthesis and stereochemical assignment of the C1–C10 fragment of nystatin A1
✍ K.C. Nicolaou; Kyo Han Ahn 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 284 KB

Compound 8 representing fhe Ct-CtO fragment of nystafin At has been synthesized from nystafin Af by degradation and by total synthesis. Comparison of the two samples revealed the 3R, 5R, 7R stereochemistry for the three nystafin A I centers. Nystatin At (I)1 is a clinically used polyene macrolide