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FeCl 3 ‐Catalyzed Highly Efficient Nazarov Type Cyclization of Arylvinylcarbinols: Total Synthesis of (±)‐Dichroanal B and Related Taiwaniaquinoids †
Author(s) -
Kakde Badrinath N.,
Parida Amarchand,
Kumar Nivesh,
Mourya Abhishek,
Bisai Alakesh
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600890
Subject(s) - total synthesis , yield (engineering) , catalysis , quaternary carbon , chemistry , core (optical fiber) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , computer science , physics , telecommunications , thermodynamics
FeCl 3 ‐catalyzed cyclization of an arylvinyl carbinols has been explored for efficient synthesis of [6,5,6]‐carbotricyclic core of taiwaniaquinoids sharing an all‐carbon quaternary center at the pseudobenzylic position. The methodology works under mild conditions, in an open flask, to afford key carbotricyclic core in excellent yields. The strategy has been applied to a concise synthesis of naturally occurring taiwaniaquinoids, (±)‐dichroanal B ( 1 h ) in 10 steps from β‐cyclocitral 7 in 34.7 % overall yield.