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Deprecated: Implicit conversion from float 209.6 to int loses precision in C:\Inetpub\vhosts\kidney.de\httpdocs\pget.php on line 534 Science 2016 ; 352 (6289): 1078-82 Nephropedia Template TP
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Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade #MMPMID27230373
Brill ZG; Grover HK; Maimone TJ
Science 2016[May]; 352 (6289): 1078-82 PMID27230373show ga
Cyclase enzymes weave simple polyprenyl chains into the elaborate polycyclic ring systems of terpenes, a sequence that is often difficult to emulate under abiotic conditions. Herein we report a disparate synthetic approach to complex terpenes whereby simple prenyl-derived chains are cyclized using radical, rather than cationic, reaction pathways. This strategy efficiently forges challenging 5/8/5-fused ring systems found in numerous complex natural product classes and enabled a nine-step total synthesis of (?)-6-epi-ophiobolin N, a member of the large family of cytotoxic ophiobolin sesterterpenes. A small-molecule thiol catalyst was found to override the inherent diastereoselectivity observed during a reductive radical cascade cyclization process. This work lays the foundation for efficiently accessing historically challenging terpenoid ring systems of interest in medicinal research.