83177-79-1Relevant academic research and scientific papers
Transalpinecine and Analogues: First Total Synthesis, Stereochemical Revision and Biological Evaluation
Dehoux, Cécile,Castellan, Tessa,Enel, Morgane,André-Barrès, Christiane,Mirval, Sandra,Becq, Frédéric,Ballereau, Stéphanie,Génisson, Yves
supporting information, p. 1830 - 1834 (2019/02/09)
The first total synthesis of transalpinecine, a pyrrolizidine alkaloid extracted from Heliotropium transalpinum is reported. The concise synthetic route developed towards these unusual iminosugar-like natural compounds relies on an intramolecular Morita–Baylis–Hillman reaction. The four diastereoisomers of transalpinecine, as well as the two diastereoisomers of the parent epoxide subulacine, were prepared. 1H NMR-based stereochemical assignment of these different diastereoisomers was substantiated by quantum calculations of NMR shifts and coupling constants, allowing revision of the initially reported transalpinecine structure. One of these synthetic compounds significantly potentiates the activity of the F508del-CFTR corrector VX-809.
Synthesis of the necine bases (±)-macronecine and (±)-supinidine via an aza-ene reaction and allylsilane induced ring closure
Sarkar, Tarun K.,Hazra, Anindya,Gangopadhyay, Pulak,Panda, Niranjan,Slanina, Zdenek,Lin, Chun-Cheng,Chen, Hui-Ting
, p. 1155 - 1165 (2007/10/03)
An aza-ene reaction has been used for the first time for the synthesis of two 5-membered lactam-hydrazides, each with a built-in allylsilane terminator for further elaboration. One of the lactam-hydrazides was transformed via an allylsilane-hydrazonium io
Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis: Applications to Pyrrolizidine Alkaloids
Keck, Gary E.,Cressman, Erik N. K.,Enholm, Eric J.
, p. 4345 - 4349 (2007/10/02)
Syntheses of (+/-)-isoretronecanol, (+/-)-supinidine, (-)-dihydroxyheliotridane, and (+)-heliotridine are detailed.The key step in each case involves an intramolecular acyliminium ion cyclization onto a suitably positioned allylstannane for construction o
Cationic Cyclizations of Ketene Dithioacetals: A General Synthesis of Pyrrolizidine, Indolizidine, and Quinolizidine Alkaloid Ring Systems
Chamberlin, A.Richard,Nguyen, Hoa D.,Chung, John Y.L.
, p. 1682 - 1688 (2007/10/02)
Cyclizations of ketene dithioacetals have been applied to the synthesis of pyrrolizidine, indolizidine, and quinolizidine alkaloid ring systems.This new cationic cyclization terminator allows the efficient formation of 5-, 6-, and 7-membered heterocyclic rings, as illustrated by the preparation of 10a-e.Several of these products, available in three steps, have been converted into the known alkaloids (+/-)-supinidine, (+/-)--trachelanthamidine, (+/-)-elaeokanine A, and (+/-)-epi-lupinine.
