A Simple Synthetic Method for 2,15-Hexadecanedione from a Butadiene Telomer

Tsuji, Jiro; Kaito, Mitsumasa; Yamada, Toshiro; Mandai, Tadakatsu

doi:10.1246/bcsj.51.1915

Cited by 30 publications

(1 citation statement)

References 9 publications

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“…Hydrolysis of the ester afforded8-oxononanoic acid 55, which was subjected to Kolbe electrolysis. By this way, 1,15-hexadecanedrone 56 was obtained in a high yield (22). Cyclization of this dione a_nd hydrogenation produced muscone 57.…”

Section: C02h 53mentioning

confidence: 95%

Palladium catalysts in natural products synthesis

Tsuji

1979

Pure and Applied Chemistry

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-Two important palladium catalyzed reactions, namely oxidation of olefins to methyl ketones with PdCl2/CuCl/02 system, and telomerization of butadiene with nucleophiles catalyzed by Pd(OAc)2/PPh3 are used in key steps of natural products synthesis. Syntheses of Matsutake alcohol, lipoic acid, diplodialide, lasiodiplodin, zearalenone, 12-acetoxy-1,3-dodecadiene, cis-civetone, recifeiolide, royal jelly acid, 2,15-hexadecanedione are described.

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Section: C02h 53mentioning

confidence: 95%

Palladium catalysts in natural products synthesis

Tsuji

1979

Pure and Applied Chemistry

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Wacker Oxidation, The

2014

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Terminal alkene substrates can be converted to methyl ketone products via a palladium‐catalyzed process known as the Wacker oxidation. This process has found widespread application in targeted synthesis, since alkene substrates are easily accessed and unreactive under diverse reaction conditions substrates and the resultant carbonyl products are common precursors for diverse synthetic manipulations. This chapter covers the application of the Wacker oxidation and variations of the Wacker oxidation to various types of alkene substrates. The literature covered spans the inception of the reaction in 1959 through November 2012. A discussion of the current mechanistic understanding is presented, emphasizing considerations that are relevant to synthetic application, including how the nature of the alkene substrate and nucleophiles other than water are proposed to influence the mechanistic pathways and ultimately the product distribution. The “Scope and Limitations” section is separated into discussions relating to functional group tolerance, the influence of heteroatoms proximal to the alkene substrate, and Wacker‐type oxidations that do not result in carbonyl products, such as cyclization reactions and aza‐Wacker reactions. Select applications of the Wacker oxidation in total synthesis are presented, as well as a comparison to other methods and examples of experimental conditions.

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