On the relationship of topological and diastereofacial control in the Lewis acid catalyzed cyclocondensation reaction of alkoxyaldehydes with activated dienes: metal tunable asymmetric induction

1984 ◽  
Vol 106 (8) ◽  
pp. 2456-2458 ◽  
Author(s):  
Samuel J. Danishefsky ◽  
William H. Pearson ◽  
Daniel Harvey
Keyword(s):  
Lewis Acid ◽  
Asymmetric Induction ◽  
Cyclocondensation Reaction ◽  
Acid Catalyzed ◽  
Relationship Of ◽  
The Relationship

C19 quassinoid model studies: Preparation of trans-perhydroindans via a vinylogous Mukaiyama aldol – free-radical cyclization route

2004 ◽  
Vol 82 (2) ◽  
pp. 314-317 ◽  
Author(s):  
Matthew G Donahue ◽  
David J Hart
Keyword(s):  
Free Radical ◽  
Acid Treatment ◽  
Titanium Tetrachloride ◽  
Aldol Reaction ◽  
Radical Cyclization ◽  
Asymmetric Induction ◽  
Model Studies ◽  
Mukaiyama Aldol ◽  
Relationship Of ◽  
The Relationship

Aldehyde 9 was prepared in 5 steps from 3,5-dimethylbenzoic acid. Treatment of 9 with ketene acetals 10 and 19 and titanium tetrachloride gave free-radical cyclization substrates 11 and 20 in 67% and 51% yields, respectively. Tri-n-butylstannane-mediated cyclization of 11 and 20 gave trans-perhydroindans 14 and 21 in 60% and 63% yields, respectively. The relationship of these studies to an approach to C19 quassinoids is discussed.Key words: vinylogous Mukaiyama aldol reaction, free-radical cyclization, trans-perhydroindans, C19 quassinoids, 1,2-asymmetric induction.

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