Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ 9-THC

Emma L. Pearson; Nicholas Kanizaj; Anthony C. Willis; Michael N. Paddon-Row; Michael S. Sherburn

doi:10.1002/chem.201001176

Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ ⁹-THC

Emma L. Pearson, Nicholas Kanizaj, Anthony C. Willis, Michael N. Paddon-Row, Michael S. Sherburn

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

(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.

Original language	English
Pages (from-to)	8280-8284
Number of pages	5
Journal	Chemistry - A European Journal
Volume	16
Issue number	28
DOIs	https://doi.org/10.1002/chem.201001176
Publication status	Published - 26 Jul 2010

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10.1002/chem.201001176

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title = "Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ 9-THC",

abstract = "(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.",

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year = "2010",

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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 - https://www.scopus.com/pages/publications/77954837403

U2 - 10.1002/chem.201001176

DO - 10.1002/chem.201001176

M3 - Article

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 28

ER -

Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ ⁹-THC

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