Toward the Total Synthesis of Spirastrellolide A. Part 2: Conquest of the Northern Hemisphere

✍ Scribed by Alois Fürstner; Michaël D. B. Fenster; Bernhard Fasching; Cédrickx Godbout; Karin Radkowski

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 240 KB
• Volume: 118
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200601655

✦ Synopsis

The novel antimitotic agent spirastrellolide A (1), isolated from the Caribbean sponge Spirastrella coccinea, is endowed with potent and selective phosphatase inhibitory properties. [1] Although the relative stereochemistry of each individual domain embedded into the macrocyclic frame of this marine natural product has been elucidated by spectroscopic means, the relationship between these stereoclusters remains elusive and the absolute configuration of 1 is equally unknown. [1] Scheme 1 therefore depicts only one of 16 possible isomers that might represent the correct stereostructure of spirastrellolide A.

Intrigued by the exquisite structural complexity of this macrolide and the prospect of contributing to a synthesisdriven mapping of its promising biological profile, [2] we Scheme 1. One of the 16 possible stereostructures that might represent spirastrellolide A. Note that the relative stereochemistry within the color-coded segments has been established, whereas the stereochemical relationship between any pair of them is still unknown.