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Formal Total Synthesis of (−)-Apicularen A via Transannular Conjugate Addition

✍ Scribed by Hilli, Ferdows; White, Jonathan M.; Rizzacasa, Mark A.

Book ID
120256515
Publisher
American Chemical Society
Year
2004
Tongue
English
Weight
125 KB
Volume
6
Category
Article
ISSN
1523-7060

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Synthesis of the core of apicularen A by
Synthesis of the core of apicularen A by transannular conjugate addition
✍ Ferdows Hilli; Jonathan M. White; Mark A. Rizzacasa 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 311 KB

The synthesis of the core of the myxobacteria metabolite apicularen A by a novel transannular 1,4-addition is described. The key step involved acid mediated transannular conjugate addition of the C13 hydroxyl into the a,b-unsaturated ketone in macrolactone 18 to provide the trans-pyranone 19 and the