Organic synthesis, Chirality (chemistry), Chiral pool synthesis

SYNFACTS Highlights in Current Synthetic Organic Chemistry. SYNFACTS, 2016, 12(08), 0863. .

Biosynthetic machinery for 4-methyloxazoline

The first total synthesis of the biologically significant bis-indole alkaloid dragmacidin D (5) has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Following this crucial sequence, a succession of meticulously controlled final events was developed leading to the completion of the natural product.

SYNFACTS Highlights in Current Synthetic Organic Chemistry. SYNFACTS, 2016, 12(3), 0307. .

Seeing and touching a single 1-nm-sized synthetic molecular ...

is there an asymmetric method which will give exclusively a single enantiomer, I did not think so. Chiral pool approach will certainely provide a single isomer of choice

It better be called relay chiral pool synthesis….on a lighter note!I would just go with “enantioselective total synthesis of XYZ”

Hepworth, Lorna; France, Scott; Hussain, Shahed; Both, Peter; Turner, Nicholas; Flitsch, Sabine. De Novo Enzyme Cascades in Whole Cells for the Synthesis of Chiral Cyclic Amines.” ACS Catalysis, 2017, 7, 2920-2925.

Chiral pool synthesis - WikiVisually


The Baran group seems to utilize the chiral pool whenever feasible for natural product synthesis. But they do use asymmetric catalyst to begin routes too. They’re also not above making racemates. So I guess their not swimming in the pool non-stop, but more dipping the toes in when it suits them.
I think their (-)-fischerindole synthesis began with carvone oxide.

Asymmetric synthesis - SlideShare

Depends how fast and cheap you want your building blocks. If you are in business of synthesizing 1 mg of marine monster, just enough so that you can take carbon NMR spectra, write up and graduate, you will pick the quickest easiest route to your building blocks and have the grant agency worry about the costs. But if you are in a pharma process group optimizing a synthetic route into a scalable practical process, you will probably spend a lot of time trying to optimize methodology for the building blocks. Asymmetric transformations are great but you first need to develop assay fpor ee and you may then spend several months just testing commercially available ligands/metal pre-catalysts/additives for one synthetic step