A bidirectional synthesis of spiroacetals via Rh(ii)-catalysed C–H insertion

  • Romain J. Lepage, Jonathan M. White, Mark J. Coster
  • Chemical Communications, January 2017, Royal Society of Chemistry
  • DOI: 10.1039/c7cc00459a

What is it about?

Molecules where two rings are joined together through a single atom are known as spirocyclic compounds. A particular type, called spiroacetals, are common in biologically-active from nature. We show, for the first time, an efficient new method for making spiroacetals from simple, non-cyclic starting materials.

Why is it important?

Spiroacetals are exciting molecular scaffolds for discovering new drugs. Our method takes simple non-cyclic precursors and, by using small amounts of certain catalysts, converts them into spiroacetals with 3-dimensional structures that make them potentially useful building blocks for drug discovery.

Perspectives

Associate Professor Mark J Coster
Griffith University

This paper is one of my proudest basic science achievements. It started with an idle wondering about whether these types of compounds could be made "backwards" compared to how they had been synthesised in the past. Although the seed of the idea was planted more than ten years ago, it took time to mature, and the end result is, in many respects, much better than the original idea. I particularly enjoyed getting my hands dirty in the lab to play with aspects of this project during a fantastic period of study leave at the Memorial Sloan-Kettering Cancer Center (MSKCC) with Prof. Derek Tan.

Read Publication

http://dx.doi.org/10.1039/c7cc00459a

The following have contributed to this page: Associate Professor Mark J Coster