Efficient synthesis of cis- and trans-3,4-dihydroxy-3,4-dihydromollugin.
An efficient synthesis of naturally occurring compounds isolated from Pentas longiflora, cis-3,4-dihydroxy-3,4-dihydromollugin 2, and trans-3,4-dihydroxy-3,4-dihydromollugin 3 is described. The O-protected mollugins were dihydroxylated using OsO4 to achieve the corresponding cis-dihydroxy derivatives in excellent yield. The synthesis of trans-3,4-dihydroxy-3,4-dihydromollugin was achieved using Oxone in good yield. A mechanism for the formation of cis-3,4-dihydroxymollugin acetonide from the reaction of mollugin with Oxone is proposed.
Mudiganti
Naga Venkata Sastry
NV
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium.
Claessens
Sven
S
Habonimana
Pascal
P
De Kimpe
Norbert
N
D032061:Galium / Q000737:chemistry*; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C470808:3,4-dihydroxy-3,4-dihydromollugin; D009285:Naphthoquinones; D011714:Pyrans