Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal 
Synthesis of (+)-Aspicilin

Schaubach, Sebastian; Michigami, Kenichi; Fürstner, Alois

doi:10.1055/s-0035-1562381

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Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin

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Schaubach, Sebastian
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Michigami, Kenichi
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Faculty of Pharmaceutical Sciences, Hokkaido University;

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Schaubach, S., Michigami, K., & Fürstner, A. (2017). Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin. Synthesis, 48(1), 202-208. doi:10.1055/s-0035-1562381.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-B4BE-1

Abstract

1,3-Enynes are hardly amenable to trans-hydrometalation reactions, because they tend to bind the standard ruthenium catalysts too tightly. However, catalysts comprising a [Cp*Ru–Cl] unit allow such compounds to be used, provided they contain an OH group next to the triple bond. This aspect is illustrated by a formal synthesis of the lichen-derived macrolide aspicilin. The required macrocyclic enyne precursor was formed by an efficient ring-closing alkyne metathesis reaction.