Journal of Organic Chemistry p. 5401 - 5409 (2013)
Update date:2022-08-04
Topics:
Yadav, Saroj
Taylor, Carol M.
(2S,4R)-2-Amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α,β-unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into peptides, a truly orthogonal protecting group scheme was developed, encompassing an allyloxycarbonyl (Alloc) carbamate for Nα, a tert-butyl ester for the δ-COOH, an acetol ester for the α-COOH, and a tert- butyldimethylsilyl ether for the γ-hydroxy group of Ahad.
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Doi:10.1021/ol401208t
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(2018)Doi:10.1016/S0040-4039(00)79971-0
(1994)Doi:10.1002/chem.201203243
(2013)Doi:10.1002/ejoc.201201033
(2013)Doi:10.1021/jm00099a005
(1992)