Synthesis of 1-amino-3-[(dihydroxyboryl)methyl]-cyclobutanecarboxylic acid as a potential therapy agent
A novel boronated aminocyclobutanecarboxylic acid (1) was synthesized for potential use in boron neutron capture therapy. Starting from the readily available 3-(bromomethyl)cyclobutanone ketal (4), several synthetic routes to 1 were evaluated. After sever
Kabalka, George W.,Yao, Min-Liang
p. 8280 - 8286
(2007/10/03)
An efficient route to 3-substituted cyclobutanone derivatives
An efficient route to 3-(hydroxymethyl)cyclobutanone acetals via a [2+2] cycloaddition reaction is reported. The dramatic effect of different diol acetals on benzyl deprotection is discussed. Efficient synthesis of two synthetically useful intermediates, 3-methylenecyclobutanone acetal and 3-(bromomethyl)cyclobutanone, are provided.
Kabalka, George W.,Yao, Min-Liang
p. 1879 - 1881
(2007/10/03)
Synthesis of 2,4-methanoproline analogues via an addition-Intramolecular substitution sequence
A new two-step synthetic approach toward 3-(chloromethyl)cyclobutanone is described and used in the synthesis of 2,4-methanoproline analogues. The key step consists of a reversible addition of hydrogen cyanide onto the imines 12 in 50-74% yield under conditions that allow ring closure. 2-Alkyl-2-azabicyclo [2.1.1]hexane-1-carbonitriles 19, synthesized in four steps, can also be converted to the corresponding amines.
Rammeloo, Thomas,Stevens, Christian V.,De Kimpe, Norbert
p. 6509 - 6513
(2007/10/03)
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