Total synthesis of d,l-quassin

1991 ◽  
Vol 69 (5) ◽  
pp. 853-855 ◽  
Author(s):  
Nada Stojanac ◽  
Zdenek Valenta
Keyword(s):  
Total Synthesis ◽  
Key Words ◽  
Ammonium Hydroxide ◽  
Enol Ether ◽  
Key Steps

The completion of the total synthesis of d,l-quassin 1 is described. Key steps are a facile intramolecular acylation of a protected cyanohydrin carbanion (4 → 5), a selective deprotonation with trioctyl methyl ammonium hydroxide leading to the removal of HCN from 8, and the unusual sequence 5 → 12 in which the ring C enol ether of 5 is converted selectively into ring C diosphenol of 12. Key words: quassin, synthesis, selective base, diosphenols, acylation.

Synthesis of (+/−) arthrographol

1991 ◽  
Vol 69 (12) ◽  
pp. 1909-1916 ◽  
Author(s):  
William A. Ayer ◽  
Peter A. Craw
Keyword(s):  
Total Synthesis ◽  
Key Words ◽  
Pinus Contorta ◽  
Lodgepole Pine ◽  
Single Step ◽  
Side Chain ◽  
Phenyl Sulfide ◽  
Blue Stain ◽  
Subsequent Elimination ◽  
Key Steps

A total synthesis of (+/−) arthrographol (1) in seven steps from vanillin is reported. Key steps in the synthesis are a single-step conversion of 5-allylvanillin (2) into the benzofuranmethanol 6, alkylation of the chloride 25 with the lithium anion of crotyl phenyl sulfide to give the sulfide 26, and formation of the 1(E),3(E)-1,3-pentadienyl side chain of arthrographol (1) via oxidation of the sulfide 26 and subsequent elimination of phenylsulfenic acid. The synthetic (+/−) arthrographol (1) inhibits the growth of Ophiostoma clavigerum (Robin.-Jeff. & Davids.) Harrington, the most pathogenic of the fungi associated with the blue stain disease of lodgepole pine (Pinus contorta Dougl. var latifolia Engelm.). Key words: arthographol, alkylation, 2-butenyl phenyl sulfide, polyketide.

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 First Total Synthesis of Artekeiskeanol A, C and Altissimacoumarin D

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 49-54 ◽  
Author(s):  
Anil Talakokkula ◽  
Karunakar Baikadi ◽  
A. Narsaiah
Keyword(s):  
Total Synthesis ◽  
Oxidation Reactions ◽  
Total Syntheses ◽  
Riley Oxidation ◽  
Key Steps

The total syntheses of artekeiskeanol A and C, and altissimacoumarin D have been achieved. The syntheses commenced from commercially available starting materials, 2,4-dihydroxybenzaldehyde and geraniol. The key steps involve Wittig and Riley oxidation reactions.

Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent

2019 ◽  
Vol 17 (31) ◽  
pp. 7325-7329
Author(s):  
Naoyuki Shimada ◽  
Kenji Fukuhara ◽  
Sari Urata ◽  
Kazuishi Makino
Keyword(s):  
Total Synthesis ◽  
Phenylboronic Acid ◽  
Total Syntheses ◽  
Key Steps

Total synthesis of seminolipid was accomplished via regioselective protection using 2,6-bis(trifluoromethyl)phenylboronic acid followed by regioselective trichloroethyl-protected sulfation as key steps.

scholarly journals Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

2018 ◽  
Vol 16 (33) ◽  
pp. 5979-5986 ◽  
Author(s):  
Arun K. Ghosh ◽  
Hannah M. Simpson ◽  
Anne M. Veitschegger
Keyword(s):  
Total Synthesis ◽  
Transfer Hydrogenation ◽  
Enantioselective Total Synthesis ◽  
Key Steps ◽  
Enantioselective Syntheses

Enantioselective syntheses of decytospolides are described using an Achmatowicz rearrangement, transfer hydrogenation and Friedel–Crafts acylation as the key steps.

Concise asymmetric total synthesis of bruceolline J

2015 ◽  
Vol 2 (5) ◽  
pp. 548-551 ◽  
Author(s):  
Dattatraya H. Dethe ◽  
Vijay Kumar B
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Asymmetric Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

Concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J.

scholarly journals Total Synthesis of Mycalisine B

Marine Drugs ◽  
2019 ◽  
Vol 17 (4) ◽  
pp. 226 ◽  
Author(s):  
Haixin Ding ◽  
Zhizhong Ruan ◽  
Peihao Kou ◽  
Xiangyou Dong ◽  
Jiang Bai ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Large Scale ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Key Steps

The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3–d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions.

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