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Total Synthesis and Structural Revision of a Harziane Diterpenoid

preprint
submitted on 05.08.2019 and posted on 06.08.2019 by Moritz Honig, Erick Carreira
The first total synthesis of nominal harziane diterpenoid is disclosed, whose spectral characteristics did not match those of the reported natural product. Stereochemical analysis and subsequent synthesis of the epimeric tertiary alcohol led to reassignment of configuration of the natural product. At the heart of the synthesis is an enyne cycloisomerization that sets a key quaternary stereocenter within a cyclobutane with high diastereocontrol. The route features strategies for the synthesis of the highly congested 6–5–7–4 carbon skeleton characteristic of the caged harziane diterpenoids.

Funding

SSCI

History

Email Address of Submitting Author

carreira@org.chem.ethz.ch

Institution

ETH Zurich

Country

Switzerland

ORCID For Submitting Author

0000-0003-1472-490X

Declaration of Conflict of Interest

No conflict of interest

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in Angewandte Chemie International Edition

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