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Synthesis 2017; 49(01): 202-208
DOI: 10.1055/s-0035-1562381
DOI: 10.1055/s-0035-1562381
paper
Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin
Further Information
Publication History
Received: 21 June 2016
Accepted: 21 June 2016
Publication Date:
04 July 2016 (online)
Dedicated to Prof. Dieter Enders on the occasion of his 70th birthday
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.
Key words
alkyne metathesis - enynes - hydrostannation - molybdenum alkylidynes - natural products - ruthenium - trans-reductionSupporting Information
- Copies of spectra of new compounds for this article is available online at http://dx.doi.org/10.1055/s-0035-1562381.
- Supporting Information
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For syntheses of the enantiomer, see: