Concise Synthesis of the Terpene Core Structure of Suaveolindole Through a Time-Economic Route

Synlett ◽  
2021 ◽  
Author(s):  
Hiroki Tanimoto ◽  
Kazuki Tojo ◽  
Tsumoru Morimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Claisen Rearrangement ◽  
Core Structure ◽  
Side Chain ◽  
Unsaturated Ester ◽  
Synthetic Route ◽  
Carbon Side Chain

The terpene core structure of suaveolindoles was synthesized through a concise route in a time-economical manner. A scalable synthetic route from pulegone delivered the desired α,β,γ,δ-unsaturated ester in a brief period. By way of Eschenmoser-Claisen rearrangement, carbon side chain moiety at the crowded double-allylic position was introduced stereoselectively.

Experiments directed towards the synthesis of anthracyclinones. VII. Model studies with allyl naphthalenyl ethers

1983 ◽  
Vol 36 (4) ◽  
pp. 803 ◽  
Author(s):  
IK Boddy ◽  
RC Cambie ◽  
G Dixon ◽  
PS Rutledge ◽  
PD Woodgate
Keyword(s):  
Claisen Rearrangement ◽  
Side Chain ◽  
Model Studies ◽  
Chain Isomerization

The Claisen rearrangement of some allyl naphthalen-1-yl ethers has been examined, together with methods for modification of the resulting 2-ally1 side chain. Isomerization of the C-allyl substituent to a prop-1-enyl group followed by ozonolysis gives a formyl derivative, while ozonolysis of a 2-(2-methylprop-2-enyl) moiety or mercuriation of a 2-(2-chloroprop-2-enyl) substituent leads to an acetonyl derivative. Treatment of phenols with iodine(I) acetate and an excess of silver(I) acetate gives 4-hydroxyaryl acetates, probably via dienone intermediates.

scholarly journals Effects of mrpigG on Development and Secondary Metabolism of Monascus ruber M7

2020 ◽  
Vol 6 (3) ◽  
pp. 156
Author(s):  
Li Li ◽  
Fusheng Chen
Keyword(s):  
Biosynthetic Pathway ◽  
Gene Deletion ◽  
The Other ◽  
Side Chain ◽  
Asian Countries ◽  
Monascus Ruber ◽  
Monascus Pigments ◽  
The World ◽  
Carbon Side Chain ◽  
Yellow Pigments

Monascus pigments (MPs) have been used as food colorants for several centuries in Asian countries and are now used throughout the world via Asian catering. The MP biosynthetic pathway has been well-illustrated, but the functions of a few genes, including mrpigG, in the MP gene cluster are still unclear. In the current study, in order to investigate the function of mrpigG in M. ruber M7, gene deletion (ΔmrpigG), complementation (ΔmrpigG::mrpigG) and overexpression (M7::PtrpC-mrpigG) mutants were successfully obtained. The morphologies and biomasses, as well as the MP and citrinin production, of these mutants were analyzed. The results revealed that the disruption, complementation and overexpression of mrpigG showed no apparent defects in morphology, biomass or citrinin production (except MP production) in ΔmrpigG compared with M. ruber M7. Although the MP profiles of ΔmrpigG and M. ruber M7 were almost the same—with both having four yellow pigments, two orange pigments (OPs) and two red pigments (RPs)—their yields were decreased in ΔmrpigG to a certain extent. Particularly, the content of rubropunctatin (an OP) and its derivative rubropunctamine (an RP) in ΔmrpigG, both of which have a five-carbon side chain, accounted for 57.7%, and 22.3% of those in M. ruber M7. On the other hand, monascorubrin (an OP) and its derivative monascorubramine (an RP), both of which have a seven-carbon side chain, were increased by 1.15 and 2.55 times, respectively, in ΔmrpigG compared with M. ruber M7. These results suggest that the MrPigG protein may preferentially catalyze the biosynthesis of MPs with a five-carbon side chain.

An Efficient Two-Step Protocol for the Isoprenylation of Xanthone at the C2 Position Starting from 1-Fluoroxanthone Derivative

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1423-1429
Author(s):  
Takashi Matsumoto ◽  
Yuuki Fujimoto ◽  
Chisato Furukawa ◽  
Kanae Takahashi ◽  
Miho Mochizuki ◽  
...  
Keyword(s):  
Silica Gel ◽  
Room Temperature ◽  
Claisen Rearrangement ◽  
High Yield ◽  
Side Chain ◽  
Snar Reaction

The SNAr reaction of 1-fluoroxanthone derivatives with alkoxide of 1,1-dimethylallyl alcohol cleanly afforded the corresponding ethers, which have thus far been unavailable. The obtained ethers underwent the Claisen rearrangement at room temperature by treatment with silica gel in toluene. This two-step protocol provides expeditious and high-yield access to xanthones possessing isoprenyl or the related allylic side chain at the C2 position.

Asymmetric Synthesis of 2,3,6-Trisubstituted Piperidines via Baylis–Hillman Adducts and Lithium Amide through Domino Reaction

Synlett ◽  
2019 ◽  
Vol 31 (06) ◽  
pp. 600-604 ◽  
Author(s):  
Mateo M. Salgado ◽  
Alejandro Manchado ◽  
Carlos T. Nieto ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Domino Reaction ◽  
Amino Acid Derivative ◽  
Side Chain ◽  
Lithium Amide ◽  
Stereochemical Control ◽  
Asymmetric Michael Addition ◽  
Polysubstituted Piperidines

A convenient asymmetric synthesis of methyl (2S,3S,6R)-6-(4-fluorophenyl)-2-(4-hydroxyphenyl)-piperidine-3-carboxylate is described, starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent chemoselective transformation of one of the side-chain groups allows an effective cyclization leading to biologically interesting polysubstituted piperidines in which the 2,6-aryl groups could be attached sequentially.

ChemInform Abstract: A New Synthetic Route to (3R,4S)-3-Hydroxy-4-phenylazetidin-2-one as a Taxol Side Chain Precursor.

ChemInform ◽  
2010 ◽  
Vol 29 (34) ◽  
pp. no-no
Author(s):  
C. E. SONG ◽  
S. W. LEE ◽  
E. J. ROH ◽  
S. LEE ◽  
W.-K. LEE
Keyword(s):  
Side Chain ◽  
Synthetic Route

Concise Synthesis of Potential 4-Hydroxy-5-fluoropentyl Side-Chain Metabolites of Four Synthetic Cannabinoids

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 517-520 ◽  
Author(s):  
Jakob Wallgren ◽  
Anders Rexander ◽  
Erik Vestling ◽  
Huiling Liu ◽  
Johan Dahlén ◽  
...  
Keyword(s):  
Synthetic Cannabinoids ◽  
Parent Drug ◽  
Cb1 Receptor ◽  
Reference Standards ◽  
Urinary Biomarkers ◽  
Drug Intake ◽  
Side Chain ◽  
Urinary Biomarker ◽  
Synthetic Route ◽  
Extensive Metabolism

Synthetic cannabinoids are a group of compounds that act on the CB1 receptor and are used illicitly as substitutes for cannabis. Given the rapid and extensive metabolism of synthetic cannabinoids, urinary biomarkers are essential if proof of drug intake is to be obtained in forensic laboratories. To identify good biomarker candidates, the metabolism of synthetic cannabinoids must be studied and reference standards need to be acquired. Studies on the metabolism of synthetic cannabinoids containing a terminally fluorinated pentyl side chain have shown that hydroxylation can occur at the four position of the side chain. This makes the 4-hydroxy-5-fluoropentyl side-chain metabolite a good urinary biomarker for proving intake of the corresponding parent drug, as this compound cannot be formed from its nonfluorinated analogue. Here, a concise synthetic route to the 4-hydroxy-5-fluoropentyl side-chain metabolites of the synthetic cannabinoids STS-135, MAM-2201, AM-2201, and XLR-11 is reported.

scholarly journals Deletion ofGPI7, a Yeast Gene Required for Addition of a Side Chain to the Glycosylphosphatidylinositol (GPI) Core Structure, Affects GPI Protein Transport, Remodeling, and Cell Wall Integrity

1999 ◽  
Vol 274 (21) ◽  
pp. 15251-15261 ◽  
Author(s):  
Abdellah Benachour ◽  
György Sipos ◽  
Isabelle Flury ◽  
Fulvio Reggiori ◽  
Elisabeth Canivenc-Gansel ◽  
...  
Keyword(s):  
Cell Wall ◽  
Protein Transport ◽  
Core Structure ◽  
Cell Wall Integrity ◽  
Side Chain ◽  
Yeast Gene
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