Journal
ORGANIC LETTERS
Volume 14, Issue 16, Pages 4042-4045Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol300954s
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Funding
- Deutsche Forschungsgemeinschaft [STA 634/1-3]
- Fonds der Chemischen Industrie
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The first synthesis of (-)-heronapyrrole C, the enantiomer of a unique farnesylated 2-nitropyrrole natural product is described. With none of the chiral centers of heronapyrrole C originally assigned, we proposed the most likely natural configuration on the basis of a putative biosynthetic pathway. The key step of the synthesis is a biomimetic polyepoxide cyclization cascade to establish the bis-THF moiety. Thus, (-)-heronapyrrole C is synthesized in eight steps from commercially available starting materials.
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