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Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone.

ABSTRACT: A rhodium-catalyzed intramolecular reductive aldol-type cyclization is described to give β-hydroxylactones with high diastereoselectivities. The stereoselectivity of this cyclization is highly solvent dependent and can give syn- or anti-β-hydroxylactones with high diastereoselectivity. This methodology was also applied to the synthesis of a chiral necic acid lactone which is a structural component of the pyrrolizidine alkaloid monocrotaline.

SUBMITTER: Isoda M

PROVIDER: S-EPMC9727276 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone.

Isoda Motoyuki M Sato Kazuyuki K Kameda Kenta K Wakabayashi Kana K Sato Ryota R Minami Hideki H Karuo Yukiko Y Tarui Atsushi A Kawai Kentaro K Omote Masaaki M

Beilstein journal of organic chemistry 20221202

A rhodium-catalyzed intramolecular reductive aldol-type cyclization is described to give β-hydroxylactones with high diastereoselectivities. The stereoselectivity of this cyclization is highly solvent dependent and can give <i>syn</i>- or <i>anti</i>-β-hydroxylactones with high diastereoselectivity. This methodology was also applied to the synthesis of a chiral necic acid lactone which is a structural component of the pyrrolizidine alkaloid monocrotaline. ...[more]

PMID: 36530534

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