Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure

descriptionPublicationkeyboard_double_arrow_right Article 01 Jul 2009 English Publisher:WileyJournal:Helvetica Chimica Acta, volume 92, pages 1,404-1,412 (issn: 0018-019X, eissn: 1522-2675,

Authors: Hee Jin Lee; Yong Rok Lee; Sung Hong Kim;

doi: 10.1002/hlca.200900014

Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure

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Abstract

AbstractAn efficient and concise synthesis of the biologically interesting (+)‐machaeriol B (2) and its enantiomer 5 was accomplished from O‐phenylhydroxylamine (7) in four steps (Scheme 2). In addition, the first total synthesis of natural (+)‐machaeriol C (3) and its enantiomer 6 was achieved from the readily available ester 15 in eight steps (Scheme 4). The key strategies in the syntheses of 2 and 5 involved benzofuran formation through a [3,3]‐sigmatropic rearrangement and trans‐hexahydrodibenzopyran formation by a domino aldol‐type/hetero‐Diels–Alder reaction. In the case of 3 and 6, the key steps were stilbene formation by a Horner–Wadsworth–Emmons reaction and trans‐hexahydrodibenzopyran formation by domino reactions.

Related Organizations

Yeungnam University
Korea (Republic of)
Korea Basic Science Institute
Korea (Republic of)

6 Research products, page 1 of 1

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Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure

Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure

6 Research products, page 1 of 1

Novel Machaeriol Analogues as Modulators of Cannabinoid Receptors: Structure–Activity Relationships of (+)-Hexahydrocannabinoids and Their Isoform Selectivities

Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ8‐THC, and Analogues

ChemInform Abstract: Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ8‐THC, and Analogues.

Short and Protecting-Group-Free Approach to the (−)-Δ8-THC-Motif: Synthesis of THC-Analogues, (−)-Machaeriol B and (−)-Machaeriol D

Antimalarial (+)-trans-Hexahydrodibenzopyran Derivatives from Machaerium multiflorum

Inside Back Cover: Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ8‐THC, and Analogues (Angew. Chem. Int. Ed. 29/2015)

Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues

ChemInform Abstract: Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues.

Short and Protecting-Group-Free Approach to the (−)-Δ⁸-THC-Motif: Synthesis of THC-Analogues, (−)-Machaeriol B and (−)-Machaeriol D

Inside Back Cover: Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues (Angew. Chem. Int. Ed. 29/2015)