Total Synthesis of (+)-6-epi-Ophiobolin A
Danny Q Thach1, Zachary G Brill1, Huck K Grover1
1Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.
Abstract:
The ophiobolin sesterterpenes are notable plant pathogens which have recently elicited significant chemical and biological attention because of their intriguing carbogenic frameworks, reactive functionalities, and emerging anticancer profiles. Reported herein is a total synthesis of (+)-6-epi-ophiobolin A in 14 steps, a task which addresses construction of the synthetically challenging spirocyclic tetrahydrofuran motif as well as several other key stereochemical problems. This work demonstrates a streamlined synthetic platform to complex ophiobolins leveraging disparate termination modes of a radical polycyclization cascade for divergent elaboration and functionalization.
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