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Spiculoic acid A   

14 June 2006 5,448 views 5 Comments

Spiculoic_acid_2.jpg
Baldwin, Kirkham and Lee. Chem. Comm., 2006, Advance Article. DOI: 10.1039/b607035c5

Not just the total synthesis here, but also the assignment of the absolute configuration, Jack Baldwin et al. have used a really nice DA to assemble the 6,5 system. Starting back at the aldehyde, a Wittig olefination completed the tethered acyclic substrate for the DA, which spontaneously cyclised at 100 ºC. Nice way to construct two quaternary centres!
Spiculoic_acid.jpg

This completed the carbocyclic skeleton of the natural product, which required relatively few steps to deliver the desired compound.

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