First total synthesis of mosin B.
[figure: see text] The first total synthesis of mosin B and a diastereomer was accomplished using asymmetric desymmetrization of the sigma-symmetric diol and the Nozaki-Hiyama-Kishi reaction as the key steps. The THF core segment was stereoselectively constructed employing a stereodivergent synthesis starting from a common intermediate, 4-cyclohexene-1,2-diol, based on a desymmetrization strategy. By virtue of these synthetic results, it is suggested that the absolute configuration is 1a.
Maezaki
N
N
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka, 565-0871, Japan.
Kojima
N
N
Sakamoto
A
A
Iwata
C
C
Tanaka
T
T
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism; D014197:Trees / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C107769:mosin B