Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and 
Application to a Formal Synthesis of Tubelactomicin A

Sommer, Heiko; Fürstner, Alois

doi:10.1021/acs.orglett.6b01431

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Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A

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

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

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Citation

Sommer, H., & Fürstner, A. (2016). Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A. Organic Letters, 18(13), 3210-3213. doi:10.1021/acs.orglett.6b01431.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-A57A-A

Abstract

Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)₂ and Ph₂As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A.