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Photoassisted access to enantiopure conformationally locked ribofuranosylamines spiro-linked to oxazolidino-diketopiperazines.

ABSTRACT: N-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.

SUBMITTER: Nandurkar NS

PROVIDER: S-EPMC3625677 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Photoassisted access to enantiopure conformationally locked ribofuranosylamines spiro-linked to oxazolidino-diketopiperazines.

Nandurkar Nitin S NS Kumar N N Bhuvan NN Mukhina Olga A OA Kutateladze Andrei G AG

ACS combinatorial science 20121204 1

N-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. ...[more]

PMID: 23157463

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