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Literature DB >> 22188422

Total synthesis of halichondrin C.

Akihiko Yamamoto¹, Atsushi Ueda, Paul Brémond, Paolo S Tiseni, Yoshito Kishi.

Abstract

The first total synthesis of halichondrin C has been completed, highlighted by development of the synthetic method to construct the C8-C14 polycycle. Cr-mediated coupling reactions are used seven times to form a new C-C bond. The acid stability of halichondrin C is studied, demonstrating that the macrolactone stabilizes the C8-C14 polycycle, relative to the one present in the C1-C16 model.

Entities: Chemical

Mesh：

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Year: 2011 PMID： 22188422 DOI： 10.1021/ja2108307

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

6 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

Total synthesis of halichondrin C.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. A unified strategy for the total syntheses of eribulin and a macrolactam analogue of halichondrin B.

3. Toward Generalization of Iterative Small Molecule Synthesis.

4. On the proposed structures and stereocontrolled synthesis of the cephalosporolides.

5. Turning Spiroketals Inside Out: A Rearrangement Triggered by an Enol Ether Epoxidation.

6. Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.