Total Synthesis of (+)-SCH 351448: Efficiency via Chemoselectivity and Redox-Economy Powered by Metal Catalysis

2016/06/23 by Gang Wang, Michael J. Krische · 22 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Asymmetric Synthesis and Catalysis #Biosynthesis #Catalysis #Chemistry #Chemoselectivity #Combinatorial chemistry #Enantioselective synthesis #Functional group #Ionophore #Marine Sponges and Natural Products #Natural product #Organic chemistry #Polyketide #Redox #Stereocenter #Stereochemistry #Synthetic Organic Chemistry Methods #Total synthesis

paper · doi:10.1021/jacs.6b04917

published in Journal of the American Chemical Society 138(26), 8088-8091 (American Chemical Society)

openalex publication_date 2016/06/23 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/05

Abstract

The polyketide natural product (+)-SCH 351448, a macrodiolide ionophore bearing 14 stereogenic centers, is prepared in 14 steps (LLS). In eight prior syntheses, 22-32 steps were required. Multiple chemoselective and redox-economic functional group interconversions collectively contribute to a step-change in efficiency.

Citations

• Asymmetric Transition Metal-Catalyzed Allylic Alkylations
• Strategic efficiency — The new thrust for synthetic organic chemists
• Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis
• Analysis of the reactions used for the preparation of drug candidate molecules
• Prevention of Undesirable Isomerization during Olefin Metathesis
• Macrocyclization by Ring‐Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations
• The SREBP Pathway: Regulation of Cholesterol Metabolism by Proteolysis of a Membrane-Bound Transcription Factor
• The Atom Economy—A Search for Synthetic Efficiency

Cited by

• Carbonyl allylation [wikipedia]

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