SYNTHESIS/SYNLETT Best Paper Awards 2023

Abstract

Thieme Chemistry and the editors of SYNTHESIS and SYNLETT present the "[SYNTHESIS/SYNLETT Best Paper Awards](https://www.thieme.de/de/thieme-chemistry/journals-synthesis-synlett-best-paper-awards-72162.htm)" to honor outstanding research in chemical synthesis. In this Thieme Cheminar, our speakers will present their research related to their award-winning articles which can be read [here](https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-1941-8680) and [here](https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-1912-3216).Our line-up:- Takaaki Sato (Japan) – “Total Synthesis and Anti-inflammatory Activity of Stemoamide-Type Alkaloids” - Santanu Mukherjee (India) – “Breaking Symmetry: Reaction Development Application to Complex Targets”Don't miss this opportunity to gain insights from leading scientists and learn about the latest advances in synthetic chemistry. RSVP above to save your spot!Breaking Symmetry: Reaction Development & Application to Complex TargetsHuman minds are fascinated by symmetrical objects, and we admire the challenges in constructing them. In contrast to the physical world, we live in, creating symmetry in the molecular world is a relatively simple task. It is the daunting asymmetry in molecules that often challenges the chemists. Breaking symmetry to generate asymmetry, known as desymmetrization, is a remarkably powerful strategy for building molecular complexity. Successful implementation holds the potential to forge multiple stereogenic centers, even away from the reaction site, in a single step. During the past few years, we have developed a number of organocatalytic enantioselective desymmetrization reactions, including a formal C-H alkylation. This talk will be primarily confined to the enantioselective formal C-H alkylation and its applications to the synthesis of complex targets.Total Synthesis and Anti-inflammatory Activity of Stemoamide-Type AlkaloidsThe stemoamide-type alkaloids have received considerable attention due to recent biological studies involving anti-inflammatory effects such as LPS-induced acute lung injury in mice. However, the structural complexity including pentacyclic scaffold prevents demonstration of the structural activity relationship. We achieve the collective total synthesis of the stemoamide-type alkaloids based on three key methods: 1) chemoselective assembly of five-membered rings, 2) stereodivergent construction of totally-substituted butenolides, and 3) direct oxidation of pyrrolidines. These methods enabled us to determine the systematic SAR, revealing that the pentacyclic framework including the totally substituted butenolide is crucial for anti-inflammatory activities.