A remarkably simple, highly efficient, and stereoselective synthesis of steroids and other polycyclic systems. Total synthesis of estra-1,3,5(10)-trien-17-one via intramolecular capture of o-quinodimethanes generated by cheletropic elimination of sulfur dioxide

1980 ◽  
Vol 45 (8) ◽  
pp. 1463-1470 ◽  
Author(s):  
K. C. Nicolaou ◽  
W. E. Barnette ◽  
P. Ma
Keyword(s):  
Sulfur Dioxide ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Highly Efficient

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 Stereocontrolled total synthesis of (+)-vinblastine

2003 ◽  
Vol 75 (1) ◽  
pp. 29-38 ◽  
Author(s):  
Satoshi Yokoshima ◽  
T. Ueda ◽  
S. Kobayashi ◽  
A. Sato ◽  
Takeshi Kuboyama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Radical Cyclization ◽  
Critical Coupling ◽  
Efficient Manner ◽  
Complete Control ◽  
Highly Efficient ◽  
Indole Synthesis

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (−)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97 % yield, which could be successfully converted to (+)-vinblastine (1).

ChemInform Abstract: A HIGHLY EFFICIENT TOTAL SYNTHESIS OF (.+-.)-LYCOPODINE

1979 ◽  
Vol 10 (12) ◽  
Author(s):  
C. H. HEATHCOCK ◽  
E. KLEINMAN ◽  
E. S. BINKLEY
Keyword(s):  
Total Synthesis ◽  
Highly Efficient

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.

Silver-assisted syntheses of fused five-membered N-heterocycles

2021 ◽  
Vol 25 ◽  
Author(s):  
Navjeet Kaur ◽  
Neha Ahlawat ◽  
Yamini Verma ◽  
Pooja Grewal ◽  
Pranshu Bhardwaj ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Heterocyclic Compounds ◽  
Stereoselective Synthesis ◽  
Review Article ◽  
Highly Efficient ◽  
Work Up ◽  
Detailed Work

: The metal-mediated formation of heterocycles is one of the most emerging and essential strategies in organic chemistry. The reactions utilized previously to synthesize heterocycles were less familiar to the scientists due to their detailed work-up, expensive nature, and complex operations. The silver-assisted cyclic reactions are highly efficient for both regioselective and stereoselective synthesis of five-membered fused N-heterocyclic compounds. The applications of silver in the preparation of five-membered fused N-heterocyclic compounds are covered in this review article.

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