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A General Strategy for Construction of Both 2,6‐ cis ‐ and 2,6‐ trans ‐Disubstituted Tetrahydropyrans: Substrate‐Controlled Asymmetric Total Synthesis of (+)‐Scanlonenyne
Author(s) -
Lee Hyunjoo,
Kim Kwan Woo,
Park Janghyun,
Kim Hyoungsu,
Kim Sanghee,
Kim Deukjoon,
Hu Xiangqian,
Yang Weitao,
Hong Jiyong
Publication year - 2008
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.200705663
Subject(s) - intramolecular force , metathesis , epimer , substrate (aquarium) , stereochemistry , chemistry , scheme (mathematics) , enantioselective synthesis , halogenation , ketone , computer science , combinatorial chemistry , mathematics , organic chemistry , catalysis , polymerization , oceanography , geology , polymer , mathematical analysis
A synthetic three‐ring circus : The asymmetric total synthesis of (+)‐scanlonenyne includes a sequential epimerization and intramolecular hetero‐Michael addition for the construction of pyrano‐γ‐lactones (see scheme; DBU: 1,8‐diazabicyclo[5.4.0]undec‐7‐ene), a highly efficient one‐carbon homologation/bromination strategy, and a Weinreb ketone synthesis/cross‐metathesis protocol for the elaboration of a sensitive side chain.