A stereospecific synthesis of functionalised cyclopentene derivatives. New principle of carbon-chain lengthening.

Cossement, E.; BINAME, R.; Ghosez, Léon

doi:10.1016/s0040-4039(01)82389-3

Cited by 21 publications

(8 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…gives the enantiomerically pure N-methylamino-acid derivative 23 with the 0and N-functional groups in the desired threo-configuration. Similar conversion of cis-5-membered ring derivatives into thermodynamically more stable trans-derivatives have precedents in the literature [23][24][25][26][27][28]12). Both protecting 'I) Analogous didehydroimines have already been isolated as dimethyl (tert-buty1)silyl derivatives, for details s.…”

Section: 4mentioning

confidence: 53%

See 1 more Smart Citation

Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2S,3R,4R,6E)‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid starting from tartaric acid

Wenger¹

1983

Helvetica Chimica Acta

View full text Add to dashboard Cite

Starting from R, R-( + )-tartaric acid, the synthesis of (2 S, 3 R, 4 R, 6 E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid in 24 steps is reported. This novel amino acid is found in the cyclic undecapeptide cyclosporin A, isolated from the fungal strain Tolypocladium inflatum GAMS. Its stereospecific synthesis allowed, for the first time, the isolation and characterization of the new amino acid previously reported as the 'C-9amino acid' [I].In the (4 R)-4-butenyl-4-N-dimethyl-threonine 25 (MeBmt, in a simplified staggered projection (i) and in a Fischer projection (ii), MeNH-and OH-groups are in a threoconfiguration as it is the case in N-methyl+-threonine (iii) and the OHand CH,groups in an erythro-configuration; the double bond is trans (E)-configurated. The

show abstract

Section: 4mentioning

confidence: 53%

“…As examples: transformation of the compounds a, b, c, d, and e into the trans products ai [23], bi [24], ci [25], di [26], and ei [27], [28], respectively.…”

Section: I*)mentioning

confidence: 99%

Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2S,3R,4R,6E)‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid starting from tartaric acid

Wenger¹

1983

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…Thus, the four-membered ring opening reaction was highly favored (Scheme 6). [16] Scheme 6. Addition of NaOEt to the acetylenic ω-keto esters 1 or 7.…”

Section: Resultsmentioning

confidence: 99%

Anionic Cascade Reaction Followed by Silylative Dieckmann Cyclization: A Straightforward Route to Tricyclic Fused Ring Systems Starting from Alkynyl Esters Tethered to Bicyclo[n.2.0]alkanones

et al. 2010

View full text Add to dashboard Cite

show abstract

“…The CHC1:) layer was separated and washed with aqueous NaHSO.1. Found: C,73.71;H,7.15;N,4.%. N-Ethylbenzylidenimine Adducts 7c and 8c. The CHCI3 layer was dried (Na2S04) and concentrated to give 2.2 g (94%) of 4a as colorless needles.…”

Section: Synthesis Of the Sulfoxides 4 7-methyl-7-(phenylsulfinyl)bimentioning

confidence: 99%

Synthetic application of methyl(phenylthio)ketene. Synthesis of vicinal-substituted cyclopentene derivatives

Ishida¹,

Minami²,

Agawa³

1979

J. Org. Chem.

View full text Add to dashboard Cite

mol of phase-transfer catalyst. Solid Chloramine-T trihydrate (15.5 g, 0.0055 mol) was slowly added with stirring and cooling with a water bath. After addition was complete the water bath was removed; stirring was continued until the reaction was complete (usually 1-2 h) as ascertained by occasional monitoring by a thin-layer chromatography. The reaction mixture was washed with 200 mL of cold 5% aqueous sodium hydroxide followed by two washes with 200-mL portions of water. The dichloromethane layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude sulfilimine was recrystallized from methanol-water (9:l).General Procedure for Preparation of Oxiranes. The N -( p -tolylsulfony1)sulfilimine (3 mmol) was dissolved in 10 mL of dimethyl sulfoxide in a dry nitrogen atmosphere. After addition of 1 equiv of butyllithium in hexane the mixture was magnetically stirred for 10 min a t room temperature, and the aldehyde or ketone (3.0 mmol) was added with a syringe. The reaction mixture, after stirring a t ambient temperature for 18-20 h, was poured into 10% aqueous sodium chloride. The product was obtained by several extractions with hydrocarbon solvent, washing the combined extracts with water, drying over anhydrous sodium carbonate, and short-path distillation.Reaction of Chloramine-T with 3-Methyl-l-(phenylthio)-2-butene (4, R = Ph). Sulfide 4 (R = Ph), bp 120-122 "C (6 mm), prepared in 93% yield by alkylation of sodium benzenethiolate with l-bromo-3-methyl-2-butene in ethanol, was subjected to the general procedure given above for reaction of Chloramine-T with sulfides a t both ambient temperature and 0 "C. In each case an oil was obtained in 63 and 53% yield, respectively, which was identified as N-(l,ldimethyl-2-propenyl)-N-(pheny1thio)-p-toluenesulfonamide (6, R = Ph): 'H NMR (CDCl3) 6 1.5 (6, s), 2.3 (3, s) 4.8-6.3 (3, vinyl multiplet), 7-8 (9, Ar). Reaction of Chloramine-T with 3-Methyl-l-(methylthio)-2-butene (4, R = CHa). Sulfide 4 (R = CHa), bp 79-81 "C (77 mm), was treated with Chloramine-T according to the general procedure. The crude product was washed with ether to give the sulfilimine 5 (R = CH3) (40%): mp 73.5-75 "C; 'H NMR (CDC13) 6 1.68 and 1.72 (6, 2 s), 2.38 (3, s), 2.58 (3, s), 3.54 (2, d), 5.02 (1, t), 7-8 (4, AB quartet). These crystals were stored for several months in the refrigerator without noticeable deterioration. Evaporation of the ether extract and chromatography of the residue gave, asan oil, therearrangedproductN-(l,l-dimethyl-2-propenyl)-Ai-(methy1thio)-p-toluenesulfonamide (6,.R = CH3) (19%); 'H NMR (CDC13) 6 1.57 (6, s), 2.42 (6, s, ArMe and SMe), 4.9-6.4 (3, vinyl multiplet), 7-8 (4, AB quartet). Acknowledgment. This work was supported by a grant from the National Science Foundation. Registry No.-1 (R = Ph; R' = Me), 10330-22-0; 1 (R = Ph; R' = Ph), 13150-76-0; 1 (R = n-C&I13; R' = n-CsHls), 69745-50-2; 1 (R = Et, R' = CHzCHzOH), 69745-51-3; 1 (R = PhCH2, R' = -oxaspiro[2.5]octane, 185-70-6; cis-6-tert-butyl-l-oxaspiro[2.5]octane, 7787-78-2; trans-6-tert-bu...

show abstract

A stereospecific synthesis of functionalised cyclopentene derivatives. New principle of carbon-chain lengthening.

Cited by 21 publications

References 4 publications

Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2S,3R,4R,6E)‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid starting from tartaric acid

Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2S,3R,4R,6E)‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid starting from tartaric acid

Anionic Cascade Reaction Followed by Silylative Dieckmann Cyclization: A Straightforward Route to Tricyclic Fused Ring Systems Starting from Alkynyl Esters Tethered to Bicyclo[n.2.0]alkanones

Synthetic application of methyl(phenylthio)ketene. Synthesis of vicinal-substituted cyclopentene derivatives

Contact Info

Product

Resources

About