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Total Synthesis of (+)-6-epi-Ophiobolin?A |
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| Authors: | Danny Q Thach Zachary G Brill Huck K Grover Kenneth V Esguerra Jordan K Thompson Thomas J Maimone |
| Institution: | 1. Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720 USA
These authors contributed equally to this work.;2. Department 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. |
| Keywords: | Naturstoffe Radikalreaktionen Spirocyclen Terpene Totalsynthese |