Chimie des fragrances

Leyendecker, F.; Comte, Marie-Thérèse

doi:10.1016/s0040-4020(01)87361-0

Cited by 12 publications

(4 citation statements)

References 27 publications

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“…First, to study the regio- and the endo / exo stereoselectivity of the 1,3-dipolar cycloaddition we carried out the reaction with the known dipolarophile 8 and the known nitrone 10 . Methyl 2-phenylthioacrylate, 8 , was obtained from racemic methyl 2-bromopropionate, (±)- 2 , by reaction with sodium thiophenoxide, followed by oxidation of the resulting methyl 2-phenylthiopropionate, (±)- 3 , with NaIO 4 to give sulfoxide 6 , as a diastereoisomeric mixture of two racemic pairs (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

et al. 2008

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A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

et al. 2008

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“…( R )-2-Phenylsulfanylpropionate (9). A 11.3 g portion of finely ground K 2 CO 3 (82.0 mmol) and 4.46 mL of thiophenol (4.74 g, 43.0 mmol) were mixed in 100 mL of CH 3 CN. Within 1 h, 10.6 g of methyl ( S )- O -toluenesulfonyl lactate 29 ( 8 ) in 100 mL of CH 3 CN was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Fe(II)-Catalyzed Imidation of Allyl Sulfides and Subsequent [2,3]-Sigmatropic Rearrangement. Preparation of α-Branched N-tert-Butyloxycarbonyl (Boc)-Protected N-Allylamines

Bach

Körber

2000

J. Org. Chem.

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Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]-sigmatropic rearrangement reaction upon treatment with N-tert-butyloxycarbonyl azide (BocN3) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples). Whereas the reaction is well suited for the transformation of alpha-unbranched sulfides to alpha-branched sulfenamides, the enantiomerically pure alpha-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% ee). A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of alpha-branched amines that bear a secondary allyl substituent (five examples, 71-93% yield). This method failed for the alpha-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)3/NEt3 in CH2Cl2 (three examples, 43-62% yield).

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“…Their efforts focused specifically on devising an efficient route to the bicyclo [8.4.0]tetradecane ring system. To accomplish this, they borrowed chemistry from Leyendecker and Comte, who found that vinyl sulfoxides could serve as an effective Michael acceptor for enolates [15]. Procter's work began with the Cu-catalysed conjugate addition of Grignard reagent 2 into enone 3.…”

Section: Procter's Synthesis Of Briarane 10-membered Ring Of Solenolide Fmentioning

confidence: 99%

Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products

Moon

Harned

2018

R. Soc. open sci.

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The briarane diterpenoids are a large family of marine natural products that have been primarily isolated from gorgonian octocorals around the world. Structurally, the family is characterized by a trans-fused bicyclo[8.4.0]tetradecane ring system containing a central, stereogenic, all-carbon quaternary carbon (C1) flanked by three additional stereocentres (C2, C10, C14). Many family members have demonstrated biological activity in numerous areas, including: cytotoxicity, anti-inflammatory, antiviral, antifungal, immunomodulatory and insect control. Despite their interesting structural properties and bioactivity, the briaranes have been largely overlooked by the synthetic community. However, in recent years, several research groups have reported progress toward developing a synthetic route to these natural products. Most of these efforts have focused on the stereoselective construction of the central C1–C2–C10–C14 stereotetrad. This review will discuss the various synthetic efforts aimed at the briarane diterpenoids along with the challenges that remain.

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Chimie des fragrances

Cited by 12 publications

References 27 publications

Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

Synthesis and Absolute Configuration of Novel N,O-Psiconucleosides Using (R)-N-Phenylpantolactam as a Resolution Agent

Fe(II)-Catalyzed Imidation of Allyl Sulfides and Subsequent [2,3]-Sigmatropic Rearrangement. Preparation of α-Branched N-tert-Butyloxycarbonyl (Boc)-Protected N-Allylamines

Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products

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