An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes

Müller, S.; Liepold, Bernd; Roth, Gerald J.; Bestmann, Hans Jürgen

doi:10.1055/s-1996-5474

Cited by 777 publications

(452 citation statements)

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“…[11] The enantiomeric syn azide (13) could be accessed in an analogous manner from (R)-epoxyoctane. [10] For the alkyne subunits, syn-8a and anti-9a alcohols were oxidized under Swern conditions to afford aldehydes 14a and 15a in excellent yields and subsequent exposure of 14a to Ohira-Bestmann homologation [12] gave exclusively syn-16a in 72% yield. Due to epimerization of aldehyde 15a under the mildly basic conditions an alternative two-step Corey-Fuchs homologation [13] approach was adopted, giving 17a in 70% yield.…”

Section: Chemistrymentioning

confidence: 99%

Non‐natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors

et al. 2014

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A series of novel bis-tetrahydropyran 1,4-triazole analogues based on the acetogenin framework display low micromolar trypanocidal activities towards both bloodstream and insect forms of Trypanosoma brucei, the causative agent of African sleeping sickness. A divergent synthetic strategy was adopted for the synthesis of the key tetrahydropyran intermediates to enable rapid access to diastereochemical variation either side of the 1,4-triazole core. The resulting diastereomeric analogues displayed varying degrees of trypanocidal activity and selectivity in structure activity relationship studies.

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Section: Chemistrymentioning

confidence: 99%

Non‐natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors

et al. 2014

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“…The construction of fragment C15-C32 started by oxidative cleavage of terminal alkene 14 in presence of catalytic amounts of OsO 4 and NaIO 4 followed by Seyferth-Gilbert homologation providing alkyne 16 (90% yield). 4 Treatment of 16 with n-BuLi followed by Weinreb amide 17 provided methyl ketone 18 in 73% yield. …”

Section: Scheme 2 Synthesis Of Iodidementioning

confidence: 99%

Studies Towards the Synthesis of Goniotrionin

Ferreira¹,

Dias

2013

Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings

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“…To a solution of crude bis-aldehydes 5.6 (64.5 mg, 0.125 mmol) in methanol (3 mL) was added potassium carbonate (260.0 mg, 1.88 mmol) followed by dropwise addition of dimethyl-1-diazo-2-oxopropylphosphonate 175,176 (192 mg, 1.00 mmol in 0.5 mL of methanol). The resulting mixture was stirred for 16 h and then concentrated.…”

Section: -(5-(benzyloxy)pentyl)-34-dihydropyridin-2(1h)-one (417)mentioning

confidence: 99%