Organic letters

s eco-C/D Ring Analogues of Ergot Alkaloids. Synthesis via Intramolecular Heck and Ring-Closing Metathesis Reactions

AV Kalinin, BA Chauder, S Rakhit, V Snieckus

文献索引：Kalinin, Alexey V.; Chauder, Brian A.; Rakhit, Suman; Snieckus, Victor Organic Letters, 2003 , vol. 5, # 19 p. 3519 - 3521

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被引用次数: 47

摘要

To test the RCM protocol 2 for the construction of the seco-C/D ring framework 16, the common starting 4-bromoindole 5 was subjected to sequential Stille coupling with allyltributyltin, 18 LAH reduction, and acylation to furnish the 4-allyltryptamine 14 in 42% overall yield (Scheme 3). Treatment with Boc 2 O followed by N-allylation afforded the RCM precursor 15. Using the first-generation catalyst [(PCy 3 ) 2 (Cl) 2 Ru CHPh] 2 in refluxing CH 2 Cl 2 under syringe pump addition ...