An efficient and scalable synthesis of a persistent abscisic acid analog (+)-tetralone ABA.

The plant hormone ()-abscisic acid (ABA) is a signalling molecule found in all plants that triggers plants' responses to environmental stressors such as heat, drought, and salinity. Metabolism-resistant ABA analogs that confer longer lasting effects require multi-step syntheses and high costs that prevent their application in crop protection. To solve this issue, we have developed a two-step, efficient and scalable synthesis of (+)-tetralone ABA from ()-ABA methyl ester.

Total Synthesis of Dolabriferol C by a Highly Stereoselective One-Pot Coupling of a meso-3,7-Diketone with Two Chiral Aldehydes.

Total synthesis of the noncontiguous polypropionate dolabriferol C was achieved by retro-Claisen fragmentation of its putative contiguous precursor under mild conditions, thus establishing the former as a plausible isolation artifact. The precursor was prepared by a novel one-pot three-component bisaldol coupling of a meso (Z,Z)-bisenolate (generated in situ from a 3,7-diketone) with two enantioenriched aldehydes to set the absolute configuration of seven stereocenters in one step. The first aldol reaction proceeded with enantioselective desymmetrization of the bisenolate to produce an enantiomerically pure enolate-aldolate.

3'-(Phenyl alkynyl) analogs of abscisic acid: synthesis and biological activity of potent ABA antagonists.

We report here the synthesis and biological testing of 3'-(phenyl alkynyl) abscisic ABA analogs, a new class of potent ABA antagonists. These ABA analogs incorporate a rigid framework of eight carbon atoms attached at the 3'-carbon atom of ABA that prevents folding of the ABA analog-bound receptor required for ABA signalling. The two-step synthesis is based upon the optimized conversion of natural (S)-ABA to 3'-iodo ABA which can be coupled to phenyl acetylenes using Sonogashira conditions, or to styryl compounds through Suzuki chemistry.

On the Origin of Dolabriferol: Total Synthesis via Its Putative Contiguous Precursor.

The putative contiguous polypropionate precursor of dolabriferol was synthesized using as the key step a rationally designed enantiomer-selective aldol coupling (i.e., with kinetic resolution) of a racemic C1-C8 ketone fragment with an enantiopure C9-C15 aldehyde fragment.