ol0c02299_si_001.pdf (4.36 MB)
Total Synthesis of Thromboxane B2 via a Key Bicyclic Enal Intermediate
journal contribution
posted on 2020-08-07, 14:06 authored by Changcheng Jing, Varinder K. AggarwalA 12-step asymmetric
synthesis of thromboxane B2 (TxB2) from 2,5-dimethoxytetrahydrofuran
is described. The synthesis
employs our organocatalytic aldol reaction of succinaldehyde to give
a key bicyclic enal intermediate. From here, the synthetic strategy
involves a conjugate addition of an alkenyl side chain to the bicyclic
enal, Baeyer–Villiger oxidation, and a highly Z-selective Wittig olefination of a hemiacetal. Key to success was
minimizing redox operations and the manipulation of functional groups
in the correct order.