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Enantioselective Synthesis of (−)‐Halenaquinone
Author(s) -
Goswami Subir,
Harada Kenichi,
ElMansy Mohamed F.,
Lingampally Rajinikanth,
Carter Rich G.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805370
Subject(s) - stereocenter , enantioselective synthesis , moiety , chemistry , ring (chemistry) , furan , stereochemistry , quinone , sulfonamide , palladium , total synthesis , combinatorial chemistry , oxidative phosphorylation , catalysis , organic chemistry , biochemistry
The efficient, 12–14 step (LLS) total synthesis of (−)‐halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide‐catalyzed, Yamada–Otani reaction to establish the C6 all‐carbon quaternary stereocenter, (b) multiple, novel palladium‐mediated oxidative cyclizations to introduce the furan moiety, and (c) oxidative Bergman cyclization to form the final quinone ring.