Synthesis of (S)‑(−)-Cucurbitine and Conformation of Its Homopeptides

A chiral cyclic α,α-disubstituted α-amino acid, (S)-(−)-cucurbitine, which has a pyrrolidine ring with a chiral center at the α-position, was synthesized, and its homopeptides were prepared. (S)-(−)-Cucurbitine homopeptides with a Boc-protecting group formed helical structures with slight control of...

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Bibliographic Details
Published in:Organic letters 2021-06, Vol.23 (11), p.4358-4362
Main Authors: Yamaberi, Yuto, Eto, Ryo, Umeno, Tomohiro, Kato, Takuma, Doi, Mitsunobu, Yokoo, Hidetomo, Oba, Makoto, Tanaka, Masakazu
Format: Article
Language:English
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Summary:A chiral cyclic α,α-disubstituted α-amino acid, (S)-(−)-cucurbitine, which has a pyrrolidine ring with a chiral center at the α-position, was synthesized, and its homopeptides were prepared. (S)-(−)-Cucurbitine homopeptides with a Boc-protecting group formed helical structures with slight control of the helical screw sense to the left-handed form. The state of the pyrrolidine ring in (S)-(−)-cucurbitine was important for the control of the helical structures and helical screw sense of its homopeptides.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01291