TY - JOUR
T1 - Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction
T2 - A short total synthesis of Δ 9-THC
AU - Pearson, Emma L.
AU - Kanizaj, Nicholas
AU - Willis, Anthony C.
AU - Paddon-Row, Michael N.
AU - Sherburn, Michael S.
PY - 2010/7/26
Y1 - 2010/7/26
N2 - (Figure Presented) 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.
AB - (Figure Presented) 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.
KW - Cannabinoids
KW - Density functional calculations
KW - Diastereoselectivity
KW - Diels-alder reactions
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=77954837403&partnerID=8YFLogxK
U2 - 10.1002/chem.201001176
DO - 10.1002/chem.201001176
M3 - Article
SN - 0947-6539
VL - 16
SP - 8280
EP - 8284
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 28
ER -