scholarly journals Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

2018 ◽  
Vol 16 (5) ◽  
pp. 750-755 ◽  
Author(s):  
Pratap R. Jagtap ◽  
Ivana Císařová ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Nucleophilic Addition ◽  
Key Steps ◽  
Redox Isomerization

Three steps suffice to complete a bioinspired total synthesis of tetrahydrofuran lignans using tandem addition/isomerization/dimerization and cycloetherification reactions.

Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1–C9 and C10–C24 Fragments

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 663-675
Author(s):  
Pabbaraja Srihari ◽  
Ramakrishna Sayini
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Addition Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Nucleophilic Addition Reaction ◽  
Convergent Approach ◽  
Key Steps

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

Total Synthesis of Macaranin B

2021 ◽  
Author(s):  
Shintaro Matsumoto ◽  
Akio Aoyama ◽  
Shinnosuke Wakamori ◽  
Hidetoshi Yamada
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Oxidative Coupling Reaction ◽  
Naturally Occurring ◽  
Key Steps

Abstract This study describes the total synthesis of macaranin B, a naturally occurring ellagitannin containing 1-O-galloyl and 3,6-O-macaranoyl groups in an axial-rich D-glucose. The Key steps of the synthesis include an oxidative coupling reaction of galloyl groups with 1,2,4-orthoacetylglucose moiety and oxa-Michael addition/elimination using an orthoquinone monoketal. This facilitates the construction of the macaranoyl group and the first total synthesis of macaranin B.

Total synthesis of wikstrol A and wikstrol B

2019 ◽  
Vol 17 (35) ◽  
pp. 8206-8213 ◽  
Author(s):  
Kui Lu ◽  
Ming Li ◽  
Yuna Huang ◽  
Yuanyuan Sun ◽  
Zhi Gong ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

The first total synthesis of wikstrol A and wikstrol B was achieved via Sharpless asymmetric dihydroxylation, Sonogashira and rhodium-catalyzed oxidative coupling as key steps.

Total synthesis of I3,II8-biapigenin and ridiculuflavone A

2017 ◽  
Vol 4 (4) ◽  
pp. 578-586 ◽  
Author(s):  
Kui Lu ◽  
Ke Yang ◽  
Xiaoliang Jia ◽  
Xing Gao ◽  
Xia Zhao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Key Steps

The first total synthesis of I3,II8-biapigenin and ridiculuflavone A was achieved via Sonogashira and rhodium-catalyzed oxidative coupling as the key steps.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

Eight‐Step Total Synthesis of Phalarine by Bioinspired Oxidative Coupling of Indole and Phenol

2019 ◽  
Vol 131 (18) ◽  
pp. 6135-6139 ◽  
Author(s):  
Lei Li ◽  
Kuo Yuan ◽  
Qianlan Jia ◽  
Yanxing Jia
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

Sign in / Sign up

Export Citation Format

Share Document