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Total Synthesis of the Resveratrol Oligomers (±)‐Ampelopsin B and (±)‐ϵ‐Viniferin
Author(s) -
Lindgren Anders E. G.,
Öberg Christopher T.,
Hillgren J. Mikael,
Elofsson Mikael
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501486
Subject(s) - chemistry , resveratrol , epimer , total synthesis , organic chemistry , stereochemistry , biochemistry
The total synthesis of the resveratrol dimers (±)‐ampelopsin B and (±)‐ϵ‐viniferin is reported. Highlights of the approach include the use of cyclopropylmethyl groups to protect aromatic alcohols. This group allows an acid promoted three‐step, one‐pot deprotection–epimerization–cyclization of an advanced intermediate to give (±)‐ampelopsin B. An important advantage with our strategy is the possibility of synthesizing analogs to these natural products to further study the chemistry and biology of resveratrol oligomers.