co3001296_si_001.pdf (4.49 MB)
Photoassisted Access to Enantiopure Conformationally Locked Ribofuranosylamines Spiro-Linked to Oxazolidino-Diketopiperazines.
journal contribution
posted on 2013-01-14, 00:00 authored by Nitin
S. Nandurkar, N. N. Bhuvan Kumar, Olga A. Mukhina, Andrei G. KutateladzeN-Furoylated l-threonine-, serine-, or cysteine-based
aminoacetals are coupled with o-aminoketones or aldehydes
to offer rapid access to diverse enantiopure polyheterocycles possessing
conformationally locked aminoglycoside-containing molecular scaffolds.
The key step involves photogeneration of azaxylylenes which undergo
[4 + 4] or [4 + 2] cycloadditions to the tethered furoyl pendants.