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Synfacts 2016; 12(08): 0767
DOI: 10.1055/s-0035-1562705
DOI: 10.1055/s-0035-1562705
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (−)-6-epi-Ophiobolin N
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. Juli 2016 (online)
Significance
The ophiobolin family of sesterpenes is characterized by a fused 5-8-5 ring system. Brill, Grover, and Maimone developed a radical cascade cyclization to assemble this ring system, culminating in the total synthesis of (−)-6-epi-ophiobolin N. The complete synthesis is remarkably short for a sesterterpene, merely requiring nine linear steps.
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Comment
Commencing from farnesol, cyclization precursor 5 could be accessed in four steps. The central radical cascade gave the fused carbon skeleton of the target molecule in 56% yield. TADDOL-derived thiol 6 was found to be crucial to favor the correct stereochemistry at C15. The natural product was obtained after four additional steps.
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