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Regioselective Inter‐ and Intramolecular Formal [4+2] Cycloaddition of Cyclobutanones with Indoles and Total Synthesis of (±)‐Aspidospermidine
Author(s) -
Kawano Mizuki,
Kiuchi Takaaki,
Negishi Shoko,
Tanaka Hiroyuki,
Hoshikawa Takaya,
Matsuo Junichi,
Ishibashi Hiroyuki
Publication year - 2013
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.201206734
Subject(s) - cycloaddition , regioselectivity , intramolecular force , computer science , chemistry , stereochemistry , catalysis , organic chemistry
This way and that way : A formal [4+2] cycloaddition between various cyclobutanones and indoles proceeded efficiently under Lewis acid catalysis (see scheme; PG = protecting group). The regioselectivity of the reaction could be controlled in such a way that each of the two possible regioisomers of a cycloaddition product could be synthesized selectively. The usefulness of this reaction for the total synthesis of hydrocarbazole natural products was demonstrated.