التفاصيل البيبلوغرافية
| العنوان: |
Stereoselective Domino Semipinacol‐Schmidt Reaction: Diastereoselective Synthesis of 7 a‐epi‐(+)‐Lepadiformine C and Formal Synthesis of 7 a‐epi‐(−)‐Lepadiformine A. |
| المؤلفون: |
Puppala, Manohar, Gore, Sangram, Eyong, Kenneth O., Baskaran, Sundarababu |
| المصدر: |
European Journal of Organic Chemistry; 5/12/2023, Vol. 26 Issue 19, p1-8, 8p |
| مصطلحات موضوعية: |
SCHMIDT reaction, RING formation (Chemistry) |
| مستخلص: |
A concise approach has been developed for the diastereoselective synthesis of the azatricyclic core of (−)‐7 a‐epi‐lepadiformine A (8 a) and (−)‐7 a‐epi‐lepadiformine C (8 b) using stereoselective domino semipinacol‐Schmidt reaction as a key step. In presence of TiCl4, the oxaspiropentane‐azide derivatives underwent stereoselective domino cyclization to furnish the corresponding angularly fused azatricyclic cores in very good yields. Moreover, azatricyclic core of (−)‐7 a‐epi‐lepadiformine A has also been realized, in a stepwise manner, through the intramolecular Schmidt reaction of azido‐spirocyclobutanone intermediate. The synthetic utility of domino semipinacol‐Schmidt reaction is further shown in the diastereoselective synthesis of (+)‐7 a‐epi‐lepadiformine C (7). [ABSTRACT FROM AUTHOR] |
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| قاعدة البيانات: |
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