Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

2020 ◽  
Vol 85 (7) ◽  
pp. 5122-5130
Author(s):  
Kajsa Lood ◽  
Bernd Schmidt
Keyword(s):  
Total Synthesis ◽  
Olefin Metathesis ◽  
Stereoselective Synthesis ◽  
Conjugated Polyenes ◽  
Carbonyl Olefination

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.

Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

scholarly journals Enantioselective Total Synthesis of the Archaeal Lipid Parallel GDGT-0

2021 ◽  
Author(s):  
Isaac D. Falk ◽  
Bálint Gál ◽  
Ahanjit Bhattacharya ◽  
Jeremy H. Wei ◽  
Paula V. Welander ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Self Assembly ◽  
Stereoselective Synthesis ◽  
Membrane Lipids ◽  
Biophysical Properties ◽  
Limited Access ◽  
Enantioselective Total Synthesis ◽  
Polar Groups ◽  
Tetraether Lipid ◽  
Significant Interest

Archaeal glycerol dibiphytanyl glycerol tetraethers (GDGT) are some of the most unusual membrane lipids identified in nature. These amphiphiles are the major constituents of the membranes of numerous <i>Archaea</i>, some of which are extremophilic organisms. Due to their unique structures, there has been significant interest in studying both the biophysical properties and the biosynthesis of these molecules. However, these studies have thus far been hampered by limited access to chemically pure samples. Herein, we report a concise and stereoselective synthesis of the archaeal tetraether lipid GDGT-0 and the synthesis and self-assembly of derivatives bearing different polar groups.

ChemInform Abstract: Olefin Metathesis Based Approach to Diversely Functionalized Pyrrolidizidines and Indolizidines; Total Synthesis of (+)-Monomorine.

ChemInform ◽  
2009 ◽  
Vol 40 (21) ◽  
Author(s):  
Giordano Lesma ◽  
Alessia Colombo ◽  
Alessandro Sacchetti ◽  
Alessandra Silvani
Keyword(s):  
Total Synthesis ◽  
Olefin Metathesis

Recent results toward the stereoselective synthesis of biologically active natural products

2007 ◽  
Vol 79 (2) ◽  
pp. 163-172 ◽  
Author(s):  
Luiz C. Dias ◽  
Luciana G. de Oliveira ◽  
Paulo R. R. Meira
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Cell Cultures ◽  
Stereoselective Synthesis ◽  
Animal Cell ◽  
Biologically Active ◽  
Asymmetric Total Synthesis ◽  
Callystatin A ◽  
Animal Cell Cultures ◽  
Active Natural

This paper describes the convergent and stereocontrolled asymmetric total synthesis of (+)-crocacins C and D, potent inhibitors of animal cell cultures and several yeasts and fungi, and (-)-callystatin A, a potent antitumor polyketide.

scholarly journals Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

2020 ◽  
Vol 16 ◽  
pp. 670-673
Author(s):  
Jan Geldsetzer ◽  
Markus Kalesse
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Vinyl Bromide ◽  
Type Coupling ◽  
Chiral Centers

The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.

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