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Total Synthesis of (+)‐6‐ epi ‐Ophiobolin A
Author(s) -
Thach Danny Q.,
Brill Zachary G.,
Grover Huck K.,
Esguerra Kenneth V.,
Thompson Jordan K.,
Maimone Thomas J.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201913150
Subject(s) - total synthesis , chemistry , combinatorial chemistry , tetrahydrofuran , stereochemistry , computational biology , nanotechnology , biology , organic chemistry , materials science , solvent
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.