Download PDF
Synfacts 2016; 12(08): 0767
DOI: 10.1055/s-0035-1562705
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (−)-6-epi-Ophiobolin N

Contributor(s):
Erick M. Carreira
,
Johannes Boshkow
Brill ZG, Grover HK, Maimone TJ * University of California, Berkeley, USA
Enantioselective Synthesis of an Ophiobolin Sesterterpene via a Programmed Radical Cascade.

Science 2016;
352: 1078-1082
CrossrefPubMedGoogle Scholar
Further Information

Publication History

Publication Date:
19 July 2016 (online)

 
 PDF Download Permissions and Reprints

Key words

(−)-6-epi-ophiobolin N - sesterterpene - radical cascade cyclization

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.


#

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.


#
#


   Permissions and Reprints