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Bioinspired Adventures in the Total Synthesis of Mixed Polyketide–Nonribosomal Peptide Natural Products
B. Nay,* M. Zaghouani, B. Laroche, S. Prévost, X.-W. Li, A. Ear, N. Riache
in Strategies and Tactics in Organic Synthesis, Vol. 13 (2017), M. Harmata (Ed.), Academic Press-Elsevier, pp. 55-80, DOI: 10.1016/B978-0-12-811790-3.00003-1.
Abstract: This account will describe some synthetic achievements obtained in our group over a period of nearly 10 years, working on natural products derived from the polyketide synthases–nonribosomal peptide synthetases (PKS–NRPS) biosynthetic pathways. We drew synthetic inspiration from biosynthetic hypotheses in an attempt to access the diversity and complexity of these natural products from linear intermediates properly functionalized to undergo multiple cyclizations. After an introduction on the biological origin and significance of PKS–NRPS compounds, we will describe a one-pot process to synthesize polyunsaturated 3-acylated tetramic acids, colored pigments found in the Myxomycetes Leocarpus fragilis. Then our work on polycyclic fungal products will be presented, starting with pyrrocidines and hirsutellones, which share an intriguing strained paracyclophane macrocycle. The biosynthetic cyclization mechanism of pyrrocidines was investigated by the use of isotopic labeling, while a formal synthesis of hirsutellones was inspired by related biosynthetic hypotheses. The chapter will end with a short account on our synthetic work on cytochalasins.