Construction of the Bicyclic Core Structure of the Enediyne Antibiotic Esperamicin-A1 in Either Enantiomeric Form from (-)-Quinic Acid

…, T Skrydstrup, H Audrain, A Chiaroni…

文献索引：Ulibarri, Gerardo; Nadler, William; Skrydstrup, Troels; Audrain, Helene; Chiaroni, Angele; et al. Journal of Organic Chemistry, 1995 , vol. 60, # 9 p. 2753 - 2761

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被引用次数: 43

摘要

Employed as a common chiral starting material,(-1-quinic acid (7) was converted in a concise manner to both enantiomers of the P, y-unsaturated ketone 12. On the one hand,(+)- 12 was obtained by stereospecific borohydride reduction of the conjugated ketone intermediate 9, transketalization, and oxidation of the derived homoallylic alcohol using the Dess-Martin periodinane reagent. Alternatively, dehydration of the tertiary alcohol 13 and ...