Studies Directed toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis)

1994 ◽  
Vol 59 (11) ◽  
pp. 3055-3063 ◽  
Author(s):  
Pier F. Cirillo ◽  
James S. Panek
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
System A ◽  
Ab Ring

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.

ChemInform Abstract: An Asymmetric Route to the Conanine BCDE Ring System. A Formal Total Synthesis of (+)-Conessine.

ChemInform ◽  
2010 ◽  
Vol 28 (8) ◽  
pp. no-no
Author(s):  
M. E. KOPACH ◽  
A. H. FRAY ◽  
A. I. MEYERS
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
System A

An Asymmetric Route to the Conanine BCDE Ring System. A Formal Total Synthesis of (+)-Conessine

1996 ◽  
Vol 118 (41) ◽  
pp. 9876-9883 ◽  
Author(s):  
Michael E. Kopach ◽  
Andrew H. Fray ◽  
A. I. Meyers
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
System A

Studies toward the total synthesis of eletefine: an efficient construction of the AB ring system

2010 ◽  
Vol 51 (42) ◽  
pp. 5585-5587 ◽  
Author(s):  
Jeremy A. Cody ◽  
Ijaz Ahmed ◽  
Douglas J. Tusch
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
Efficient Construction ◽  
Ab Ring
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