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

Submitting author affiliation:
Setsunan University, Hirakata, Osaka, Japan

Beilstein Arch. 2022, 202272. https://doi.org/10.3762/bxiv.2022.72.v1

Published 16 Sep 2022

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Rhodium-catalyzed intramolecular reductive aldol-type cyclization was described to give β-hydroxylactones with high diastereoselectivities. This cyclization gave syn- or anti-form β-hydroxylactones selectively by changing the solvent. Furthermore, the synthesis of a chiral necic acid lactone was also described which is a part of structural component of pyrrolizidine alkaloid monocrotaline that is used for the preparation of pulmonary hypertension pathological model in rats.

Keywords: intramolecular reductive aldol cyclization; β-hydroxylactone; rhodium catalyst; necic acid lactone

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Isoda, M.; Sato, K.; Kameda, K.; Wakabayashi, K.; Sato, R.; Minami, H.; Karuo, Y.; Tarui, A.; Kawai, K.; Omote, M. Beilstein Arch. 2022, 202272. doi:10.3762/bxiv.2022.72.v1

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