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Pei Gan Myles W. Smith Nathaniel R. Braffman Scott A. Snyder 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(11):3689-3694
Although the Diels–Alder reaction has long been utilized for the preparation of numerous heterocycles, opportunities to extend its power remain. Herein, we detail a simple, modular, and robust approach that combines various amines regioselectively with 4,6‐dichloropyrone to create substrates which, under appropriate conditions, can directly deliver varied indolines and hydroindolines through [4+2] cycloadditions with substitution patterns difficult to access otherwise. As an initial demonstration of the power of the strategy, several different natural products have been obtained either formally or by direct total synthesis, with efforts toward one of these—the complex amaryllidaceae alkaloid gracilamine—affording the shortest route to date in terms of linear step count. 相似文献
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Lian‐Dong Guo Xiong‐Zhi Huang Shi‐Peng Luo Wen‐Sen Cao Yuan‐Ping Ruan Jian‐Liang Ye Pei‐Qiang Huang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(12):4132-4136
The first total synthesis of the alkaloid (−)‐haliclonin A is reported. The asymmetric synthesis relied on a novel organocatalytic asymmetric conjugate addition of nitromethane with 3‐alkenyl cyclohex‐2‐enone to set the stereochemistry of the all‐carbon quaternary stereogenic center. The synthesis also features a Pd‐promoted cyclization to form the 3‐azabicyclo[3,3,1]nonane core, a SmI2‐mediated intermolecular reductive coupling of enone with aldehyde to form the requisite secondary chiral alcohol, ring‐closing alkene and alkyne metathesis reactions to build the two aza‐macrocyclic ring systems, and an unprecedented direct transformation of enol into enone. 相似文献
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