Abstract
Four stereoisomers of centrolobine, (3R,7S)-(−)-centrolobine (1), (3S,7S)-(−)-epi-centrolobine (2), (3S,7R)-(+)-centrolobine (3), and (3R,7R)-(+)-epi-centrolobine (4) have been achieved in an efficient manner in 24–28% overall yield over 9–10 linear steps starting from cheap and commercially available 4-methoxybenzaldehyde following chemoenzymatic protocol. The key features of this synthetic protocol are enzymatic resolution, cross-metathesis (CM), and our own developed tandem isomerization followed by C–O and C–C bond formation reaction.
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