Formal Synthesis of Brefeldin A from (+)-Limonen-10-ol

Formal Synthesis of Brefeldin A from (+)-Limonen-10-ol

The conversion of naturally abundant (+)-limonen-10-ol (2) into the synthetic intermediate (3) for brefeldin A is described. The cis-3, 4-disubstituted cyclopentanone (4), which was easily obtained from 2 by Rh (I)-catalyzed cyclization reaction via the 4-pentenal derivative, could be converted to t...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1985/09/25, Vol.33(9), pp.4021-4025
Hauptverfasser: UENO, KOHSHI, SUEMUNE, HIROSHI, SAEKI, SEITARO, SAKAI, KIYOSHI
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
brefeldin A
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung:The conversion of naturally abundant (+)-limonen-10-ol (2) into the synthetic intermediate (3) for brefeldin A is described. The cis-3, 4-disubstituted cyclopentanone (4), which was easily obtained from 2 by Rh (I)-catalyzed cyclization reaction via the 4-pentenal derivative, could be converted to the target compound 3 via the appropriate modification of substituents on the five-membered ring.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.33.4021