𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A Highly Efficient Synthesis of a Naphthalenoid Histamine-3 Antagonist

✍ Scribed by Yi-Yin Ku; Tim Grieme; Yu-Ming Pu; Ashok V. Bhatia

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
244 KB
Volume
351
Category
Article
ISSN
1615-4150

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

A highly efficient synthesis of the potent and selective histamine‐3 receptor antagonist 1A was accomplished in four chemical steps and a salt formation step in 36% overall yield from 6‐bromo‐2‐naphthalenol 9. The key features are a regioselective Suzuki coupling protocol for selective vinylation of 12 with potassium vinyltrifluoroborate in high yield (92%) with excellent regioselectivity (90:2) and a base‐catalyzed hydroamination reaction of 11 in an anti‐Markovnikov fashion under mild reaction conditions. An optimized copper‐catalyzed cross coupling reaction is used to incorporate the pyridazinone 4.

📜 SIMILAR VOLUMES

An Efficient Stereoselective Total Synth
An Efficient Stereoselective Total Synthesis of dl-Sesquicillin, a Glucocorticoid Antagonist
✍ Fei Zhang; Samuel J. Danishefsky 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 102 KB 👁 1 views

Sesquicillin is a C29 isoprenoid-related fermentation product isolated from Acremonium sp., strain 132-94. [1] The compound was first identified through screenings directed at the discovery of new agents that inhibit glucocorticoidinduced gene expression in suitably engineered COS-7 cells (IC 50 0.1