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

descriptionPublicationkeyboard_double_arrow_right Article 27 Apr 2018 English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 20, pages 2,964-2,966 (issn: 1523-7060, eissn: 1523-7052,

Authors: Grete Hoffmann; Armido Studer;

doi: 10.1021/acs.orglett.8b01005

pmid: 29701472

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

- Summary
- Related research
  (7)
- Metrics

tips_and_updates
Recommended

Abstract

Friedel-Crafts alkylation of resorcinols with ( S)- cis-verbenol and subsequent cyclization allows the construction of the tetrahydrodibenzopyran core of (-)-Δ8-THC which is also found in other natural products in one step. Using a benzofuryl substituted resorcinol, followed by diastereoselective hydroboration and oxidative or reductive workup, directly provides (-)-machaeriol B and D in 42% and 43% overall yields. Bromoresorcinol as a coupling partner delivers Br-THC that can be applied for late-stage diversification by Suzuki-Miyaura cross-coupling to readily access (-)-Δ8-THC analogues.

Related Organizations

University of Münster
Germany

7 Research products, page 1 of 1

Antimalarial (+)-trans-Hexahydrodibenzopyran Derivatives from Machaerium multiflorum
2001IsAmongTopNSimilarDocuments
ChemInform Abstract: Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues.
2015IsAmongTopNSimilarDocuments
Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens
2020IsAmongTopNSimilarDocuments
Novel Machaeriol Analogues as Modulators of Cannabinoid Receptors: Structure–Activity Relationships of (+)-Hexahydrocannabinoids and Their Isoform Selectivities
2021IsAmongTopNSimilarDocuments
Total Synthesis of (+)‐Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure
2009IsAmongTopNSimilarDocuments
Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues
2015IsAmongTopNSimilarDocuments
Inside Back Cover: Short and Divergent Total Synthesis of (+)‐Machaeriol B, (+)‐Machaeriol D, (+)‐Δ⁸‐THC, and Analogues (Angew. Chem. Int. Ed. 29/2015)
2015IsAmongTopNSimilarDocuments

Impact byBIP!

	citations This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	15
	popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.	Top 10%
	influence This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	Average
	impulse This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.	Top 10%

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

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

7 Research products, page 1 of 1

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

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

Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens

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

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

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

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

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

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

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