2740-00-3Relevant articles and documents
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Clemo,Ramage
, p. 2969,2971 (1932)
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Danishefsky,Dynak
, p. 1979 (1974)
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Dijkink,Speckamp
, p. 4047 (1975)
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Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids
Quevedo-Acosta, Yovanny,Jurberg, Igor D.,Gamba-Sánchez, Diego
supporting information, p. 239 - 243 (2020/01/02)
A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this method, we describe the preparation of (±)-coniceine, (±)-quinolizidine, (±)-tashiromine, (±)-epilupinine, and the core of (±)-valmerins.
Efficient and Direct Synthesis of γ-Amino-α,β-Unsaturated Amides by Catalyzed Allylic Substitution of α-Fluoroenamides: Toward to Synthesis of Hybrid Peptides and Indolizidines
Reddy, K. Harsha vardhan,Bédier, Matthieu,Bouzbouz, Samir
, p. 1455 - 1459 (2018/04/06)
A variety of γ-amino-α,β-unsaturated amides have been synthesized from readily available α-fluoroenamides precursors via an unprecedented intermolecular and intramolecular conjugative catalytic amination process. These γ-amino-α,β-unsaturated amides are useful intermediates for accessing rarely synthesized hybrid peptides, αγα sequences, and various classes of alkaloids containing a pyrrolidine ring, as illustrated by total synthesis of the indolizidine alkaloid coniceine.
Facile and short synthesis of (±) 1-hydroxy indolizidine and (±) coniceine from picolinic acid ethyl ester via cross claisen condensation
Veeraswamy,Anjaiah,Yennam, Satyanarayana,Jayashree
, p. 1667 - 1670 (2015/03/04)
New short synthesis of (±) 1-hydroxy indolizidine (4) and (±) coniceine (5) are described starting from picolinic acid ethyl ester (6). The key steps are the conversion of the picolinic acid ethyl ester into β-keto ester 7 via cross Claisen condensation and hydrogenation of the β-keto ester in to hydroxy bicyclic amide (8) using PtO2/H2.
