Total Synthesis of Thromboxane B2 via a Key Bicyclic Enal Intermediate

Changcheng Jing, Varinder K. Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

A 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.
Original languageEnglish
Pages (from-to)6505-6509
Number of pages5
JournalOrganic Letters
Volume22
Issue number16
Early online date7 Aug 2020
DOIs
Publication statusPublished - 21 Aug 2020

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