TY - JOUR A1 - Isoda, Motoyuki A1 - Sato, Kazuyuki A1 - Kameda, Kenta A1 - Wakabayashi, Kana A1 - Sato, Ryota A1 - Minami, Hideki A1 - Karuo, Yukiko A1 - Tarui, Atsushi A1 - Kawai, Kentaro A1 - Omote, Masaaki T1 - Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone JF - Beilstein Journal of Organic Chemistry PY - 2022/// VL - 18 SP - 1642 EP - 1648 SN - 1860-5397 DO - 10.3762/bjoc.18.176 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.18.176 KW - β-hydroxylactone KW - intramolecular reductive aldol cyclization KW - necic acid lactone KW - rhodium catalyst N2 - 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. ER -