TY - JOUR
T1 - Domino Reaction for the Synthesis of Polysubstituted Pyrroles and Lamellarin R
AU - Hwu, Jih Ru
AU - Roy, Animesh
AU - Panja, Avijit
AU - Huang, Wen Chieh
AU - Hu, Yu Chen
AU - Tan, Kui Thong
AU - Lin, Chun Cheng
AU - Hwang, Kuo Chu
AU - Hsu, Ming Hua
AU - Tsay, Shwu Chen
N1 - Funding Information:
For financial support, we thank the Ministry of Science and Technology (MOST, grant nos. 106-2113-M-007-011-MY2 and 107-3017-F-007-002) and the Ministry of Education (grant nos. 106N501CE1 and 107QR001I5) of R.O.C. We also thank the MOST in Taiwan to support The Featured Areas Research Center Program within the framework of the Higher Education Sprout Project through the Frontier Research Center on Fundamental and Applied Sciences of Matters. English in this manuscript has been polished by Wallace Academic Editing.
PY - 2020/8/7
Y1 - 2020/8/7
N2 - A three-component annulation reaction was developed for the synthesis of pyrroles, a class of compounds with various properties valuable to biomedical and polymer industries. Treatment of α-silylaryl triflates, Schiff bases, and alkynes generated polysubstituted pyrroles in good yields (61-86%) with regioselectivity. This domino reaction involved completion of five sequential steps in a single flask, which comprised aryne formation through 1,2-elimination, their alkylation by Schiff bases through 1,2-addition, 1,4-intramolecular proton transfer, Huïsgen 1,3-dipolar cycloaddition, and dehydrogenative aromatization. It was then successfully applied as the key step in the synthesis of the natural product lamellarin R. This new reaction represents an efficient, sustainable process for the production of chemical materials.
AB - A three-component annulation reaction was developed for the synthesis of pyrroles, a class of compounds with various properties valuable to biomedical and polymer industries. Treatment of α-silylaryl triflates, Schiff bases, and alkynes generated polysubstituted pyrroles in good yields (61-86%) with regioselectivity. This domino reaction involved completion of five sequential steps in a single flask, which comprised aryne formation through 1,2-elimination, their alkylation by Schiff bases through 1,2-addition, 1,4-intramolecular proton transfer, Huïsgen 1,3-dipolar cycloaddition, and dehydrogenative aromatization. It was then successfully applied as the key step in the synthesis of the natural product lamellarin R. This new reaction represents an efficient, sustainable process for the production of chemical materials.
UR - http://www.scopus.com/inward/record.url?scp=85090045245&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85090045245&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c01134
DO - 10.1021/acs.joc.0c01134
M3 - Article
AN - SCOPUS:85090045245
VL - 85
SP - 9835
EP - 9843
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 15
ER -