Fig. 1: Eribulin: origins, Eisai and Alphora process synthesis intermediates and α-chloroaldehyde building blocks for eribulin.
From: An α-chloroaldehyde-based formal synthesis of eribulin
A The anticancer marine natural product halichondrin B and synthetic analog eribulin. B Key building blocks used in the Eisai and Alphora process synthesis of eribulin. C Key disconnections in our proposed eribulin synthesis rely on α-chloroaldehydes generated via organocatalysis as the predominant source of chirality for the C14–C35 fragment. Red arrows depict an epoxide opening/rearrangement reaction. The green bar denotes bonds formed by chloride displacement. Blue X represents O or NBoc. PG protecting group, Piv pivalate, Boc tert-butoxycarbonyl, TBS tert-butyldimethylsilyl.
