Biomimetic synthesis of dimeric metabolite acremine G via a highly regioselective and stereoselective Diels-Alder reaction.
The dimeric metabolite acremine G was synthesized featuring a highly regioselective and stereoselective Diels-Alder reaction between a TBS-protected hydroquinone diene and a structurally related alkenyl quinone. The major endo [4 + 2] adduct slowly transforms to acremine G by the atmospheric air under the deprotection conditions (in situ generated HF).
Arkoudis
Elias
E
Department of Chemistry, University of Crete, Voutes 71003 Iraklion, Greece.
Lykakis
Ioannis N
IN
Gryparis
Charis
C
Stratakis
Manolis
M
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics / Q000379:methods; D015394:Molecular Structure; D013237:Stereoisomerism
D016227:Benzoquinones; C527633:acremine G