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Total Synthesis of (±)-Leonuketal

preprint
submitted on 20.07.2020 and posted on 20.07.2020 by Phillip Grant, Dan Furkert, Margaret Brimble
Cleavage of a C–C bond is a diversifying process in the biogenesis of seco-terpenoids that has produced fascinating molecular structures. Leonuketal is an 8,9-seco-labdane terpenoid with a unique tetracyclic structure, owing to a C–C bond cleavage event in its biosynthesis. We report the first total synthesis of leonuketal, featuring an unusual Shapiro-type reaction as part of an enabling auxiliary ring strategy, and a novel Au-catalysed spirocyclization of a b-keto(enol)lactone.

Funding

University of Auckland Doctoral Scholarship to PSG

History

Email Address of Submitting Author

d.furkert@auckland.ac.nz

Institution

University of Auckland

Country

New Zealand

ORCID For Submitting Author

0000-0001-6286-9105

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Leonuketal Rxiv

Exports