Norcysteine (Ncy) is an unnatural amino acid possessing an electronegative sulfur atom directly attached to the α-carbon atom. We describe the synthesis of Boc-d,l-Ncy(Mob)-OH, the resolution of its methyl ester, and the introduction of both d- and l-Ncy in GnRH analogues.
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Samant, White, Hong, Croston, Conn, Janovick and Rivier
200750 (9), pp 2067–2077
Abstract: A series of acyline analogues incorporating l- and d-isomers of S-arylated/alkylated norcysteines [Ncy(R), where R is 2-naphthyl, methyl, and isopropyl] at positions 1, 4, 7, and 10 were synthesized. Some of these analogues were mono- and dioxidized to ...
Abstract: An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure–enantioselectivity relationship studies and mechanistic analysis point to a dual ...
Abstract: We report the first total synthesis of the limonoid andirolide N using a 12-step sequence from commercially available materials. The final step of this route demonstrates the chemical feasibility of our biosynthetic proposal that andirolide N arises from ...
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