scholarly journals Practical Synthesis of 1,1′-Binaphthyl-2-carboxylic Acids via Side Chain Oxidation of 2-Methyl-1,1′-binaphthyls

1986 ◽  
Vol 59 (6) ◽  
pp. 2044-2046 ◽  
Author(s):  
Sotaro Miyano ◽  
Shin-ichi Okada ◽  
Toshiyuki Suzuki ◽  
Shigeru Handa ◽  
Harukichi Hashimoto
Keyword(s):  
Carboxylic Acids ◽  
Side Chain ◽  
Chain Oxidation ◽  
Practical Synthesis

scholarly journals Stereochemistry of the side chain oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha-triol in man.

1980 ◽  
Vol 255 (4) ◽  
pp. 1483-1485
Author(s):  
R.F. Hanson ◽  
P. Szczepanik-Van Leeuwen ◽  
G.C. Williams
Keyword(s):  
Side Chain ◽  
Chain Oxidation ◽  
Alpha 7

scholarly journals Practical synthesis of 4-aryl- and 4-heteroarylazetidin-2-ones: applications in the synthesis of the Taxol® side chain

1994 ◽  
Vol 72 (10) ◽  
pp. 2131-2136 ◽  
Author(s):  
Allan W. Rey ◽  
Robert Droghini ◽  
James L. Douglas ◽  
Purushotham Vemishetti ◽  
Susan D. Boettger ◽  
...  
Keyword(s):  
Side Chain ◽  
Staudinger Reaction ◽  
Protecting Group ◽  
Practical Synthesis

A convenient, high-yielding procedure has been developed for the kilogram-scale synthesis of (±)-cis-3-acetoxy-4-phenylazetidin-2-one (3), a β-lactam that has been used in the semi-synthesis of Taxol®. The Staudinger reaction between hydrobenzamide (5) and acetoxyacetyl chloride in the presence of a base provided the α-benzylideneiminotoluene protected β-lactam 8. Without isolation of the intermediate β-lactam, the protecting group was removed under various reductive or hydrolytic conditions. The overall yields were about 80%. The synthesis of other (±)-cis-4-aryl- and 4-heteroarylazetidin-2-ones by this methodology has also been accomplished. These compounds are of value for the synthesis of 3′-Taxol® side-chain analogs and their preparation demonstrates the generality of this approach.

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