Asymmetric synthesis of bioactive alkaloids from Amaryllidaceae

Abstract

A new route towards the diasteroselective synthesis of (+)-maritidine, a bioactive alkaloid from Amaryllidaceae, has been proposed. In our approach, an intramolecular Heck reaction was used to form the quaternary stereocentre C10b driven by the stereochemical information at C4a of the precursor. Allylic oxidation of intermediate 3.25 followed by diasteroselective reduction, introduced the alcohol at C3 with the correct stereochemistry. An advanced intermediate (3.29) in the synthesis of (+)-maritidine was produced, and routes to complete the total synthesis were proposed.
A series of polymer-supported sulfonate ester linkers were developed for use in the resin-linker-vector (RLV) approach for the synthesis of [18F]-radiopharmaceuticals used as imaging probes in positron-emission-tomography (PET). Upon exposure of the RLV construct to [18F]-fluoride, a small quantity of [18F]-radiotracer is released in solution which is separated from the unreacted material and cleaved resin, by simple filtration. The RLV strategy was successfully applied for the synthesis of the known radiopharmaceutical O-(2-[18F]-fluoroethyl)-L-tyrosine, [18F]-FET.
A C-H activation-cyclisation sequence was used to achieve the synthesis of the Amaryllidaceae alkaloid oxoassoanine as well as a phenanthridinoid analogue, part of potential non-charged dual reactivators of acetylcholinesterase (AChE) poisoned by organophosphorous (OP) nerve agents.

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ORCID for Richard C.D. Brown: orcid.org/0000-0003-0156-7087

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