Vitamin‐B 12 ‐katalysierte C,C‐Bindungsverknüpfung: Synthese von Jasmonaten via sequentielle Radikal‐Reaktion
1994; Wiley; Volume: 77; Issue: 1 Linguagem: Inglês
10.1002/hlca.19940770112
ISSN1522-2675
AutoresStephan Busato, Rolf Scheffold,
Tópico(s)Radical Photochemical Reactions
ResumoVitamin‐B 12 ‐Catalyzed C, C‐Bond Formation: Synthesis of Jasmonates via Sequential Radical Reaction The Cbl‐catalyzed electroreduction of 3‐(2′‐bromo‐1′‐ethoxyethoxy)cyclopenten ( 1a ) in presence of 1‐cyanovinyl‐acetate ( 8 ) gave, in a sequential radical reaction (5‐ exo‐trig ‐cyclization of 1a followed by addition to 8 ), 1‐cyano‐2‐(2′‐ethoxy‐hexahydro‐2′ H ‐cyclopenta[ b ] furan‐4′‐yl)ethyl acetate ( 10a ). This intermediate was transformed to methyl jasmonate ( 7 ; four steps) and epituberolide ( 9 ; three steps) in 20 and 31% yield, respectively, from cyclopent‐2‐en‐l‐ol.
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