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Total Synthesis

All articles tagged with #total synthesis

science1 month ago

Stereochemistry-Smart Ketone Editing via Pd(II)/Pd(IV) Decarboxylative Rearrangement

A Nature study reveals a palladium(II)/Pd(IV)–catalyzed decarboxylative semi-pinacol rearrangement that converts β-hydroxy carboxylic acids into ketones through a concerted six-membered Pd(IV) chelate, enabling precise stereochemical control (migrating carbon preserves configuration while the α-carbon inverts) and high migrating-group selectivity for unsymmetrical ketones. The method applies broadly to cyclic and acyclic ketones and aldehydes, avoids hazardous diazo reagents, and is showcased in a concise total synthesis of rupestine D, highlighting its potential as a versatile carbon-skeleton-editing tool.

via Nature|
#decarboxylative-rearrangement#organic-synthesis#palladium-catalysis
The enduring craft of total synthesis: Nicolaou reflects on a lifetime of molecules
science3 months ago

The enduring craft of total synthesis: Nicolaou reflects on a lifetime of molecules

In a preview interview ahead of his 80th birthday, K. C. Nicolaou reflects on a career that defined modern total synthesis, detailing his approach to assembling complex natural products, the challenges overcome, and the impact of his work on drug discovery and chemical biology, as shared with Stephanie Greed in Nature Reviews Chemistry.

via Nature|
#chemistry#interview#natural-products
Decade-long breakthrough: first total synthesis of bacteriochlorophyll a achieved in lab
science5 months ago

Decade-long breakthrough: first total synthesis of bacteriochlorophyll a achieved in lab

After nine years of work, a US team led by Jonathan Lindsey at NC State achieved the first total synthesis of bacteriochlorophyll a, a four-stereocentre macrocycle central to bacterial photosynthesis. The route uses an asymmetric Michael addition to set stereochemistry, a Knoevenagel condensation to join halves, followed by Nazarov cyclisation and electrophilic aromatic substitution to close the macrocycle with the correct configuration. Despite Covid-related supply challenges and the death of a team member in February 2025 slowing progress, the achievement provides access to a range of photosynthetic tetrapyrroles and could be adapted to other native pigments, with plans to streamline the process and improve yields.

via Chemistry World|
#bacteriochlorophyll-a#macrocycle#photosynthesis