Total Synthesis of (±)-Strychnine

Key words

(±)-strychnine - cyclopropyl–iminium rearrangement - Diels–Alder cycloaddition - Jeffrey–Heck reaction

Significance

The heptacyclic alkaloid strychnine has been the focus of numerous synthetic efforts over the last 75 years since the first total synthesis by Woodward. In 1994, Rawal and Iwasa reported a concise, stereo-controlled total synthesis of racemic strychnine notable for its elegance.

Comment

Elaboration of starting material A to aniline C involves a cyclopropyl-iminium rearrangement. After alkylation to yield E, Diels–Alder cycloaddition gives rise to carbamate F. The Jeffrey modification of the Heck reaction yields advanced intermediate I, which is then converted to the natural product.

Publication History

Article published online:
16 February 2021