Isoformononetin → (-)-Maackiain

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]([C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:12][O:13][C:5]=2[CH:4]=1)=[O:10].[CH3:21][O:22]C1C=CC(C2C(=O)C3C=CC(O)=CC=3OC=2)=C(O)C=1.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]2[C:55](=[O:56])[C:54]3[CH:57]=[CH:58][C:59]([OH:61])=[CH:60][C:53]=3[O:52][CH:51]=2)=[CH:46][C:45]=1[OH:62].C1OC2C=C(C3C(=O)C4C=CC(O)=CC=4OC=3)C=CC=2[O:64]1>>[CH:58]1[C:59]([OH:61])=[CH:60][C:53]2[O:52][CH2:51][C@H:50]3[C:47]4[CH:46]=[C:45]5[O:62][CH2:42][O:43][C:44]5=[CH:49][C:48]=4[O:56][C@H:55]3[C:54]=2[CH:57]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C@H:9]3[O:10][C:15]4[C:14](=[CH:19][C:18]5[O:22][CH2:21][O:20][C:17]=5[CH:16]=4)[C@@:11]3([OH:64])[CH2:12][O:13][C:5]=2[CH:4]=1

Participants

Reactant 4

HCID 3764Isoformononetin

HCID 5280448Calycosin

HCID 5280551Xenognosin B

HCID 5281805Pseudobaptigenin

Product 2

HCID 91510(-)-Maackiain

HCID 101689(+)-Pisatin

Procedure

Isoformononetin, 2′-hydroxyformononetin, 3′-hydroxyformononetin (calycosin) and pseudobaptigenin were purchased from Apin (Abingdon, UK). Maackiain and pisatin were kindly provided by Dr. H. D. VanEtten, (University of Arizona, Tucson). Maackiain glucoside and maackiain glucose malonate standards were gifts from Dr. S. Tebayashi (Kochi University, Japan). Medicarpin was from a lab collection. Other isoflavonoids were from Indofine Chemical Company (Somerville, N.J.). CO was obtained from Aldrich and all other chemicals were from Sigma (St. Louis, Mo.).