<i>Z</i>-Selective Horner−Wadsworth−Emmons Reaction of Ethyl (Diarylphosphono)acetates Using Sodium Iodide and DBU

Ando, Kaori; Oishi, Tohru; Hirama, Masahiro; Ohno, Hiroaki; Ibuka, Toshiro

doi:10.1021/jo000068x

Cited by 155 publications

(68 citation statements)

References 15 publications

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“…Table 1. A change in the base did not improve the (Z)/(E) ratio, while the modified HWE method of Ando et al, [15] which uses diarylphosphonoacetate in the presence of NaI and DBU, furnished an isomeric mixture of the ethyl crotonate 5b in a promising 80:20 (Z)/ (E) ratio. The best result, however, was obtained by the StillϪGennari [16] procedure, in which electrophilic bis(trifluoroethyl)phosphonoacetates were used.…”

Section: Synthesis Of Viridifloric β-Lactone (1a) and Its Nor Derivatmentioning

confidence: 91%

Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

2002

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Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the β-lactones 1a and 1b is based on a controlled C−C coupling by a Horner−Wadsworth−Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the δ-lactone 3b uses an enantioselective hy-

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Section: Synthesis Of Viridifloric β-Lactone (1a) and Its Nor Derivatmentioning

confidence: 91%

Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

2002

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“…LiAlH 4 and diisobutylaluminum hydride (DIBAL) were either inert or degraded the substrate, while NaBH 4 in MeOH reduced the amide moiety selectively, yet differently (!CH 2 OH) than desired. The resulting hydroxyaldehyde 8 was not purified because of its instability, and thus crude 8 was subjected to the Ando-type [21] Horner-Wadsworth-Emmons olefination with a mixture of bromophosphonates 9 a and 9 b developed for this purpose. [22] This gave hydroxybromoacrylate 10 [23] with 95 % E selectivity.…”

Section: Thomas Olpp and Reinhard Brückner*mentioning

confidence: 99%

Total Synthesis of the Light‐Harvesting Carotenoid Peridinin

Olpp

Brückner

2006

Angew Chem Int Ed

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Light work: The light‐harvesting marine C37 carotenoid peridinin was synthesized from (+)‐diethyl tartrate and (−)‐actinol. Key transformations were the differential reduction of an ester‐containing Weinreb amide, an E‐selective olefination by an Ando‐type bromophosphonate, the anti‐selective β‐elimination establishing the C1′C5 bond Z selectively, and a cis→trans isomerization of the C6′C7′ bond (see picture).

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“…14,15,18) Syntheses of the analogs 4, 5, 7, and 12 were also performed mainly by the Z-selective olefination of the corresponding aldehydes with the Ando-Emmons re- agents, 19,20) followed by the hydrolysis (Chart 1). The commercially unavailable starting aldehydes 21 and 23 were prepared according to the literature.…”

Section: Methodsmentioning

confidence: 99%

“…21,22) The trans-analog 13 was synthesized via the usual Honor-Emmons reaction. 19,20) (0.921 g, 2.28 mmol) in tetrahydrofuran (THF) (10 mL), Triton B (40% in methanol, 1.15 mL, 2.91 mmol) at −78°C under an argon atmosphere was added dropwise. After 15 min of stirring, a solution of isophthalaldehyde (16) (0.139 g, 1.04 mmol) in THF (3.5 mL) was added dropwise to the solution.…”

Section: Methodsmentioning

confidence: 99%

<i>cis</i>-Cinnamic Acid Selective Suppressors Distinct from Auxin Inhibitors

Okuda

Nishikawa

Fukuda

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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The activity of cis-cinnamic acid (cis-CA), one of the allelochemicals, in plants is very similar to that of indole-3-acetic acid (IAA), a natural auxin, and thus cis-CA has long been believed to be an analog of auxin. We have reported some structure-activity relationships studies by synthesizing over 250 cis-CA derivatives and estimating their inhibitory activities on root growth inhibition in lettuce. In this study, the compounds that showed low-or no-activity on root growth inhibition were recruited as candidates suppressors against cis-CA and/or auxin and tested for their activity. In the presence of cis-CA, lettuce root growth was inhibited; however, the addition of some cis-CA derivatives restored control-level root growth. Four compounds, (Z)-3-(4-isopropylphenyl)acrylic acid, (Z)-3-(3-butoxyphenyl)acrylic acid, (Z)-3-[3-(pentyloxy)phenyl]acrylic acid, and (Z)-3-(naphthalen-1-yl)acrylic acid were selected as candidates for a cis-CA selective suppressor they allowed the recovery of root growth from inhibition by cis-CA treatment without any effects on the IAA-induced effect or elongating activity by themselves. Three candidates significantly ameliorated the root shortening by the potent inhibitor derived from cis-CA. In brief, we have found some cis-CA selective suppressors which have never been reported from inactive cis-CA derivatives for root growth inhibition. cis-CA selective suppressors will play an important role in elucidating the mechanism of plant growth regulation.

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Z-Selective Horner−Wadsworth−Emmons Reaction of Ethyl (Diarylphosphono)acetates Using Sodium Iodide and DBU

Cited by 155 publications

References 15 publications

Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

Total Synthesis of the Light‐Harvesting Carotenoid Peridinin

<i>cis</i>-Cinnamic Acid Selective Suppressors Distinct from Auxin Inhibitors

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