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Concise and Scalable Total Syntheses of Lamellarin Z and other Natural Lamellarins
Author(s) -
Kumar Virendra,
Salam Abdus,
Kumar Dileep,
Khan Tabrez
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004008
Subject(s) - pyrrole , isoquinoline , aromatization , total synthesis , domino , chemistry , yield (engineering) , combinatorial chemistry , cycloaddition , aryl , stereochemistry , natural product , organic chemistry , materials science , catalysis , alkyl , metallurgy
Abstract An efficient construction of the central 1,2,4‐trisubstituted pyrrole core via one‐pot [3+2] cycloaddition/elimination/aromatization sequence‐based domino process and subsequent Pd‐mediated cross dehydrogenative coupling between the C−H bonds of pyrrole and the peripheral aryl rings enables rapid access to the pentacyclic coumarin‐pyrrole‐isoquinoline scaffolds which were smoothly elaborated to the targeted lamellarins alkaloids. The total synthesis of lamellarins Z and S with the highest overall yield reported till date, besides the synthesis of several other natural lamellarins have been realized in 5–6 steps with overall yields ranging from 20–27 %.