Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan

Kin-Ichi Oyama; Tadao Kondo

doi:10.1021/jo0494681

Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan

J Org Chem. 2004 Aug 6;69(16):5240-6. doi: 10.1021/jo0494681.

Authors

Kin-Ichi Oyama¹, Tadao Kondo

Affiliation

¹ Chemical Instrument Center and Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

PMID: 15287766
DOI: 10.1021/jo0494681

Abstract

We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 angstroms in CH2Cl2 and a catalytic amount of BF3 x Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4'-O-glycosylation, promoted with a combination of BF3 x Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Commelina / chemistry*
Flavonoids / chemical synthesis*
Glycosylation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oxidation-Reduction
Pigments, Biological / chemical synthesis*

Substances

Flavonoids
Pigments, Biological
flavocommelin