Total Synthesis of Pleuromutilin

2017/06/17 Hiroaki Matoba

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Pleuromutilin

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Retrosynthesis

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Gibbons’ synthesis (1)

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Gibbons’ synthesis (2)

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Gibbons’ synthesis (3)

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Problem for construction of C12 quaternary center

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Gibbons’ synthesis (4)

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Gibbons’ synthesis (5)

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Short summary

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Derivatization of preulomutilin

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Epimerization at C12 position

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12-epi-preulomutilin derivative

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Retrosynthesis

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Herzon’s synthesis (1)

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Zincate mediated 3 component coupling reaction

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Herzon’s synthesis (2)

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Herzon’s synthesis (3)

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Herzon’s synthesis (4)

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Herzon’s synthesis (5)

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Herzon’s synthesis (6)

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Regioselective reductive cyclization (1)

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Regioselective reductive cyclization (2)

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Stereoselectivity

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Herzon’s synthesis (7)

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Herzon’s synthesis (8)

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Summary

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