The Total Synthesis of Raistrickindole A.

Autor: Pham TL; School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore., Sae-Lao P; School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore., Toh HHM; School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore., Csókás D; Theoretical Chemistry Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar Tudósok krt. 2, Budapest 1117, Hungary., Bates RW; School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2022 Dec 02; Vol. 87 (23), pp. 16111-16114. Date of Electronic Publication: 2022 Nov 11.
DOI: 10.1021/acs.joc.2c02033
Abstrakt: The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an N -hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed N -hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.
Databáze: MEDLINE