Organic Chemistry

Concise syntheses of GB22, GB13 and himgaline by cross-coupling and complete reduction

Authors

Abstract

Class III neuroactive metabolites from the bark of Galbu-limima belgraveana occur in variable distribution and are not easily procured by chemical synthesis. Here we decrease the synthetic burden of himgaline to nearly one-third of the prior best (7–9 vs. 19–31 steps) by cross-coupling high fraction aromatic (FAr) building blocks followed by com-plete, stereoselective reduction to high-fraction sp3 (Fsp3) products. This short entry into GB alkaloid space allows its extensive exploration and biological interrogation.

Content

Thumbnail image of TEXT.pdf

Supplementary material

Thumbnail image of Supplementary Information v2.pdf
Supporting Information for Concise syntheses of GB22, GB13 and himgaline by cross-coupling and complete reduction
Experimental procedures, copies of NMR spectra, X-ray structure reports, full outlines of prior syntheses, and Matplotlib Python code.