The first total synthesis of (-)-ericanone was achieved in 10 steps with a 16% overall yield from p-hydroxybenzaldehyde. Notable features of this stereocontrolled approach include a Keck allylation to install the stereocenter at C3 and a 1,5-anti aldol reaction to install the hydroxyl group at C7. (C) 2012 Elsevier Ltd. All rights reserved.
A Stereodivergent Synthesis of All Stereoisomers of Centrolobine: Control of Selectivity by a Protecting-Group Manipulation
作者:Bernd Schmidt、Frank Hölter
DOI:10.1002/chem.200902053
日期:2009.11.9
Allstereoisomers of the natural product centrolobine are selectively synthesized, by starting from a common precursor. Key steps are an enantioselective allylation with enantiomerically pure allylsilanes, a tandem ring‐closing metathesis–isomerization reaction, and a Heck reaction by using an arene diazonium salt. By choosing appropriate conditions for the final deprotection step, either the cis‐configured