Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach

2014 ◽  
Vol 12 (31) ◽  
pp. 5973-5980 ◽  
Author(s):  
U. Nookaraju ◽  
Eeshwaraiah Begari ◽  
Pradeep Kumar
Keyword(s):  
Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Novel Synthesis ◽  
Key Steps ◽  
Julia Olefination

A simple and novel synthesis of (+)-monocerin was achieved from 3-buten-1-ol employing HKR, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation–cyclization 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 The total synthesis of D-chalcose and its C-3 epimer

2013 ◽  
Vol 9 ◽  
pp. 2620-2624 ◽  
Author(s):  
Jun Sun ◽  
Song Fan ◽  
Zhan Wang ◽  
Guoning Zhang ◽  
Kai Bao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Camphorsulfonic Acid ◽  
Asymmetric Dihydroxylation ◽  
Key Steps ◽  
Stereogenic Center ◽  
Hydroxy Groups

We completed a new and efficient synthesis of D-chalcose (I) and the first synthesis of its C-3 epimer (I′) in nine steps with overall yields of 23% and 24%, respectively. The key steps in the sequence were the formation of the stereocenter on C3 via Grignard reaction, the introduction of the stereogenic center on C2 by Sharpless asymmetric dihydroxylation, the protection of the C1 and C2 hydroxy groups with tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf), and the selective cleavage of the primary OTBS ether using catalytic DL-10-camphorsulfonic acid (CSA) in MeOH.

A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (−)-lentiginosine, (−)-epi-lentiginosine and (−)-dihydroxypyrrolizidine

2014 ◽  
Vol 12 (25) ◽  
pp. 4454-4460 ◽  
Author(s):  
Shruti Vandana Kauloorkar ◽  
Vishwajeet Jha ◽  
Ganesh Jogdand ◽  
Pradeep Kumar
Keyword(s):  
Total Synthesis ◽  
Pyrrolizidine Alkaloids ◽  
Starting Material ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

The total synthesis of (−)-lentiginosine, epi-1,2-lentiginosine and dihydroxypyrrolizidine is reported from an aldehyde as a starting material using organocatalysis and asymmetric dihydroxylation as key steps.

Enantioselective first total synthesis of eujavanoic acid B through organocatalyzed IMDA reaction

RSC Advances ◽  
2015 ◽  
Vol 5 (19) ◽  
pp. 14465-14469 ◽  
Author(s):  
Jayprakash Narayan Kumar ◽  
Biswanath Das
Keyword(s):  
Total Synthesis ◽  
Starting Material ◽  
Asymmetric Allylation ◽  
Key Steps ◽  
Julia Olefination

The first total synthesis of the polyketide eujavanoic acid B has been accomplished using 1,3-propane diol as the starting material and involving Maruoka asymmetric allylation, Julia olefination, HWE olefination and organocatalyzed IMDA reaction as the key steps.

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.

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.

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