Lithium triethylborohydride reduction of alkyl methanesulfonate esters

Holder, Richard W.; Matturro, Michael G.

doi:10.1021/jo00432a033

Cited by 54 publications

(13 citation statements)

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“…With robust conditions established for installing the piperidine moiety, we next turned our attention to transforming the methylene mesylate group in 91 to a methyl group (Scheme 15). Attempts to reduce 91 with lithium triethylborohydride 64 and the CuCl 2 ·2H 2 O/Li/catalytic 4,4′-di- t -butylbiphenyl system 65 failed, returning only unreacted starting material. The lack of reactivity is presumably due to the steric congestion at the neopentyl mesylate site.…”

Section: Resultsmentioning

confidence: 99%

A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids

et al. 2017

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The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C, C, and C families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these molecules by chemical synthesis, including a photochemical approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C (weisaconitine D), one C (liljestrandinine), and three C (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.

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Section: Resultsmentioning

confidence: 99%

A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids

et al. 2017

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“…This alcohol was Scheme 1. Synthesis of deuterated 5-pentylresorcinols subsequently deoxygenated following standard methodology, 18 involving mesylate formation and lithium triethylborohydride (superhydride) reduction. These two reactions were carried out without purification of the unstable mesylate intermediate 3c leading to 4c in an overall 95% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of side chain specifically deuterated (−)‐Δ⁹‐tetrahydrocannabinols

Nikas¹,

Thakur²,

Makriyannis³

2002

Labelled Comp Radiopharmac

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Summary(À)-D 9 -Tetrahydrocannabinols specifically deuterated at the n-pentyl side chain were prepared using the corresponding resorcinols as key intermediates. To obtain the deuterated resorcinols we developed conditions under which no deuterium scrambling or loss was observed. The methodology allows for the preparative scale synthesis of deuterated resorcinols and corresponding (À)-D 9 -tetrahydrocannabinols.

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“…Because of the poor yields in the reduction step, other methods for effecting the carbomethoxyl to methyl transformation were investigated. Alcohols 20 were mesylated and the mesylates reduced with lithium triethylborohydride (superhydride) (25). The only products obtained were the alcohols 20, the result of S-0 cleavage.…”

Section: A R = Ch(-0ch2ch20-)mentioning

confidence: 99%

The transformation of levopimaric acid into warburganal

Ayer¹,

Talamás²

1988

Can. J. Chem.

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The chiral resin acid levopimaric acid (1), isolated from pine oleoresin, is used as a starting material for the synthesis of (−)-warburganal (2). The synthesis proceeds via the endoperoxide of methyl levopimarate, which after ozonolysis, protection of the resulting aldehyde function, reduction, and treatment with sodium methoxide provides the tetranorditerpenoid 12a. The hemiacetal 12a is then transformed to a mixture of hemithioacetals. At this point the carbomethoxyl group at C-4 is reduced to a methyl group, and then a C-11, C-12 double bond is introduced. Ozonolysis followed by elimination of formic acid provides a mixture of olefins (27) that is hydroxylated at C-9. Removal of the protecting group then gives (−)-warburganal (2). The sequence requires 15 steps and the overall yield from levopimaric acid to warburganal is 2.7%.

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Lithium triethylborohydride reduction of alkyl methanesulfonate esters

Abstract: Figure 2. lH NMR spectra (100 MHz) of ethylmethylsulfonium 3,4-dihydro-l,4-dioxo-3-(phenylimino)-2(lif)-naphthylenylide (3) in Me2SO-de at various temperatures: (a) 32 °C, (b) 60 °C, (c) 80 °C, (d) 100 °C.

Cited by 54 publications

References 4 publications

A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids

A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids

Synthesis of side chain specifically deuterated (−)‐Δ⁹‐tetrahydrocannabinols

The transformation of levopimaric acid into warburganal

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Lithium triethylborohydride reduction of alkyl methanesulfonate esters

Abstract: Figure 2. lH NMR spectra (100 MHz) of ethylmethylsulfonium 3,4-dihydro-l,4-dioxo-3-(phenylimino)-2(lif)-naphthylenylide (3) in Me2SO-de at various temperatures: (a) 32 °C, (b) 60 °C, (c) 80 °C, (d) 100 °C.

Cited by 54 publications

References 4 publications

A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids

A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids

Synthesis of side chain specifically deuterated (−)‐Δ9‐tetrahydrocannabinols

The transformation of levopimaric acid into warburganal

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A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids

A Unifying Synthesis Approach to the C₁₈-, C₁₉-, and C₂₀-Diterpenoid Alkaloids

Synthesis of side chain specifically deuterated (−)‐Δ⁹‐tetrahydrocannabinols