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Experimental and Computational Studies into an ATPH‐Promoted exo ‐Selective IMDA Reaction: A Short Total Synthesis of Δ 9 ‐THC
Author(s) -
Pearson Emma L.,
Kanizaj Nicholas,
Willis Anthony C.,
PaddonRow Michael N.,
Sherburn Michael S.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001176
Subject(s) - intramolecular force , stereoselectivity , promotion (chess) , chemistry , tris , total synthesis , stereochemistry , computer science , combinatorial chemistry , organic chemistry , political science , catalysis , biochemistry , politics , law
Reversal of fortune : The inherent cis stereoselectivity of an intramolecular Diels–Alder reaction is reversed through promotion with aluminum tris(2,6‐diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ 9 ‐tetrahydrocannabinol (see scheme). Computational studies predict the experimental findings and shed light on the stereocontrolling influences at play in these Diels–Alder reactions.