18621-06-2Relevant articles and documents
Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids
Hall, Christopher J. J.,Goundry, William R. F.,Donohoe, Timothy J.
supporting information, p. 6981 - 6985 (2021/03/01)
For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C?C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.
The first total synthesis of discorhabdin A
Tohma, Hirofumi,Harayama, Yu,Hashizume, Miki,Iwata, Minako,Kiyono, Yorito,Egi, Masahiro,Kita, Yasuyuki
, p. 11235 - 11240 (2007/10/03)
The first stereoselective total synthesis of a potent antitumor alkaloid, discorhabdin A (1), which is a unique sulfur-containing pyrroloiminoquinone alkaloid, is described. The key step in the stereocontrolled total synthesis of 1 involves both a diaster
