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Synthetic Studies on Chartelline C: Stereoselective Construction of the Core Skeleton
Author(s) -
Iwasaki Kotaro,
Kanno Rentaro,
Morimoto Toshiharu,
Yamashita Tohru,
Yokoshima Satoshi,
Fukuyama Tohru
Publication year - 2012
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.201204726
Subject(s) - stereoselectivity , moiety , intramolecular force , amide , stereochemistry , alkylation , ring (chemistry) , chemistry , core (optical fiber) , mitsunobu reaction , trimethylsilyl , combinatorial chemistry , computer science , organic chemistry , catalysis , telecommunications
What a core‐ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β‐lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β‐lactam was controlled by a secondary hydroxy group on the ten‐membered ring. SEM=2‐(trimethylsilyl)ethoxymethyl; TBS= tert ‐butyldimethylsilyl.
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