scholarly journals A convergent total synthesis of ouabagenin

2015 ◽  
Vol 6 (6) ◽  
pp. 3383-3387 ◽  
Author(s):  
Ken Mukai ◽  
Satoshi Kasuya ◽  
Yuki Nakagawa ◽  
Daisuke Urabe ◽  
Masayuki Inoue
Keyword(s):  
Total Synthesis ◽  
Cardenolide Glycoside ◽  
Ab Ring

A convergent total synthesis of ouabagenin, an aglycon of cardenolide glycoside ouabain, was achieved by assembly of the AB-ring, D-ring and butenolide moieties.

Total Synthesis of Luotonin (Ia) and a Small Library of AB-Ring Substituted Analogues by Cascade Radical Annulation of Isonitriles.

ChemInform ◽  
2006 ◽  
Vol 37 (14) ◽  
Author(s):  
Raghuraman Tangirala ◽  
Smitha Antony ◽  
Keli Agama ◽  
Yves Pommier ◽  
Dennis P. Curran
Keyword(s):  
Total Synthesis ◽  
Ab Ring

Synthesis of 8,14-Secosteroids from (S)-(+)-Carvone

2000 ◽  
Vol 65 (7) ◽  
pp. 1173-1182 ◽  
Author(s):  
Anna I. Kotyatkina ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
Aede de Groot
Keyword(s):  
Total Synthesis ◽  
Membered Ring ◽  
Reductive Cleavage ◽  
Nitrile Oxide ◽  
Side Chain ◽  
Ene Reaction ◽  
Nitrile Oxides ◽  
Cyclic Enones ◽  
Derivatives Of ◽  
Ab Ring

A total synthesis of functionalised 8,14-seco steroids with five- and six-membered D rings is described. The synthesis is based on the transformation of (S)-carvone into a steroidal AB ring moiety with a side chain at C-9 that allowed the creation of a nitrile oxide at this position. The nitrile oxides were coupled with cyclic enones or enol derivatives of 1,3-diketones, and reductive cleavage of the obtained cycloadducts gave the desired products. The formation of a twelve-membered ring compound was observed in cycloaddition of one of the nitrile oxides with cyclopentenone as the result of an intramolecular ene-reaction followed by retroaldol reaction.

Taxane Diterpene Synthesis Studies. Part 2: Towards Taxinine—Enantiospecific Construction of an AB-ring Substructure Incorporating both Quaternary Carbon Centres and Attempts to Annulate the C-ring

2004 ◽  
Vol 57 (1) ◽  
pp. 53 ◽  
Author(s):  
Martin G. Banwell ◽  
Malcolm D. McLeod ◽  
Andrew G. Riches
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Ring System ◽  
Diels Alder ◽  
Biologically Active ◽  
Allylic Oxidation ◽  
Cope Rearrangement ◽  
Rearrangement Reaction ◽  
Ab Ring ◽  
Active Natural

In connection with efforts to develop an efficient total synthesis of the biologically active natural product taxinine 1, the enzymatically-derived and monochiral cis-1,2-dihydrocatechol 7 was converted, over several steps including a Diels–Alder cycloaddition reaction, into the bicyclo[2.2.2]octan-2-one 18. Reaction of the last compound with the organocerium reagent 22 afforded the 1,5-diene 23 which engaged in an anionic oxy-Cope rearrangement reaction to give, after C-methylation of the product enolate 25, bicyclo[5.3.1]undecenone 27 embodying the AB-ring system of target 1. Two methods for allylic oxidation of such products were developed and several unsuccessful attempts to effect a cyclization reaction so as to establish the taxane C-ring are described.

Total Synthesis of Luotonin and a Small Library of AB-Ring SubstitutedAnalogues by Cascade Radical Annulation of Isonitriles

Synlett ◽  
2005 ◽  
pp. 2843-2846 ◽  
Author(s):  
Dennis P. Curran ◽  
Raghuraman Tangirala ◽  
Smitha Antony ◽  
Keli Agama ◽  
Yves Pommier
Keyword(s):  
Total Synthesis ◽  
Ab Ring
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