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Concise Access to the Skeleton of Protoilludane Sesquiterpenes through a Photochemical Reaction Cascade: Total Synthesis of Atlanticone C
Author(s) -
Zech Andreas,
Jandl Christian,
Bach Thorsten
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201908619
Subject(s) - conrotatory and disrotatory , regioselectivity , chemistry , yield (engineering) , cascade , derivative (finance) , cascade reaction , cycloaddition , photochemistry , ring (chemistry) , carbon skeleton , natural product , stereochemistry , organic chemistry , materials science , catalysis , chromatography , economics , financial economics , metallurgy
In a single photochemical operation ( λ ≥350 nm) an easily accessible indanone derivative was converted into a structurally complex precursor of the protoilludane sesquiterpenes. The product (60 % yield) contains all 15 carbon atoms of the skeleton in the required connectivity and was transformed into the natural product atlanticone C (9 steps, 6 % overall yield). In addition, it was shown that other protoilludanes, such as Δ 6 ‐protoilludene and paesslerin A, can be prepared in a concise fashion via the photochemical key intermediate. The photochemical reaction cascade comprises an ortho photocycloaddition, a thermal disrotatory ring opening and a regioselective disrotatory [4π] photocyclization.