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Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

preprint
submitted on 12.06.2019 and posted on 13.06.2019 by Hannah E. Burdge, Takuya Oguma, Takahiro Kawajiri, Ryan Shenvi

The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.

Funding

GM122606, CHE1352587, JSPS 17J08551, Jiangsu Industrial Technology Research Institute, Shionogi & Co., Ltd.

History

Email Address of Submitting Author

rshenvi@scripps.edu

Institution

Scripps Research

Country

USA

ORCID For Submitting Author

0000-0001-8353-6449

Declaration of Conflict of Interest

No conflict of interest

Exports