Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

13 June 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

galbulimima alkaloids
cross coupling
iridium catalysis
Nickel Catalysis
siloxycyclopropane
Friedel-Crafts arylation

Supplementary materials

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Shenvi160
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