Rhodium(III)-Catalyzed Intramolecular Annulation through CH Activation: Total Synthesis of (±)-Antofine, (±)-Septicine, (±)-Tylophorine, and Rosettacin

Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope,...

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Published in	Angewandte Chemie International Edition Vol. 51; no. 37; pp. 9372 - 9376
Main Authors	Xu, Xianxiu, Liu, Yu, Park, Cheol-Min
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 10.09.2012 WILEY‐VCH Verlag Wiley
Subjects	2-pyridones Activation Alkaloids - chemical synthesis Alkaloids - chemistry Alkynes Alkynes - chemistry annulation Carbon - chemistry Catalysis Chemical reactions Chemistry Chemistry, Multidisciplinary Cyclization CH activation Esters Heterocyclic Compounds, 4 or More Rings - chemical synthesis Heterocyclic Compounds, 4 or More Rings - chemistry Hydrogen - chemistry Indoles - chemical synthesis Indoles - chemistry Indolizines - chemical synthesis Indolizines - chemistry Isoquinolines - chemistry isoquinolones Organic chemistry Oxidants Phenanthrenes - chemical synthesis Phenanthrenes - chemistry Phenanthrolines - chemical synthesis Phenanthrolines - chemistry Physical Sciences Pyridones - chemistry rhodium Rhodium - chemistry Science & Technology Stereoisomerism Synthesis Tolerances isoquinolones HIGHLY SUBSTITUTED PYRROLES INDOLIZIDINE C?H activation ALKYNES 2-pyridones ISOQUINOLONE SYNTHESIS H ACTIVATION annulation QUINOLIZIDINE ALKALOIDS BIOLOGICAL EVALUATION DIAZO OXIME ETHERS N BOND FORMATION CATALYZED OXIDATIVE COUPLING/CYCLIZATION rhodium
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ISSN	1433-7851 1521-3773 1521-3773
DOI	10.1002/anie.201204970

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Summary:	Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional‐group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant.
Bibliography:	ark:/67375/WNG-H5GZ1RRT-F ArticleID:ANIE201204970 istex:D12262FBE2168B59E0D2642931509D88C96DFACC Nanyang Technological University We gratefully acknowledge the Nanyang Technological University for the funding of this research. We thank Dr. Rakesh Ganguly for X-ray crystallographic analysis. We gratefully acknowledge the Nanyang Technological University for the funding of this research. We thank Dr. Rakesh Ganguly for X‐ray crystallographic analysis. These authors contributed equally to this work. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773 1521-3773
DOI:	10.1002/anie.201204970