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Tetrahedron Letters

Volumn 36, Issue 42, 1995, Pages 7709-7712

The solid phase synthesis of dihydro- and tetrahydroisoquinolines

(2) Meutermans, Wim D F a Alewood, Paul F a

a UNIVERSITY OF QUEENSLAND (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY;

EID: 0028784613 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(95)01569-4 Document Type: Article

Times cited : (58)

References (23)

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9
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10
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11
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- Springer-Verlag, New York & Oxford
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12
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13
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- Erickson, B.W.; Merrifield, R.B.,The Proteins ; Academic Press: New York, vol 2, 3rd edn., pp 255.

14
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- 3 at elevated temperatures.

15
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- 3Boc-protection was carried out in dioxane/water (1/1) with 1 eq. KCO and 1.1 eq. (Boc)O.
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- Gensler¹ Bluhm²

16
- 84915375421
- 3 in EtOH/water (1/1). After evaporation of the solvent, the residue is dissolved in DMF, added to chloromethylated polystyrene (crosslinked with 1% DVB; 0.75 meq./gr., 1.5 Cs-salt to 1 Cl) and heated overnight to 50 °C (s.v. = 0.31 meq/g).

17
- 84915375420
- 11 of the resin and HPLC isolation of the dimethoxyphenylalanine (s.v.= 0.31 meq/g); b. aminoacid analysis of the resin (s.v. = 0.36 meq/g).This method is less accurate then method a because of partial decomposition of dimethoxyphenylalanine during HCl treatment.

18
- 84915375419
- For HF cleavage, 300 mg of resin are mixed with 1ml of p-cresol. HF (9ml) is distilled into the reaction vessel and left stirring at 0 °C for 1h. The HF is then evaporated under vacuum, a small amount of ether is added to precipitate the product and wash out the p-cresol. The product is filtered and dissolved in methanol giving the crude cleavage mixture.

19
- 84915375418
- For deprotection 40% TFA in DCM was used (1 times 1min / 1 times 10min). The resin is then washed with DCM, DCM/MeOH (1/1) and DMF. Coupling is achieved with 4eq. of acid, 4eq. of HBTU (0.5M) and 5eq. of DIEA in DMF (10 min).

20
- 84915375417
- 3CN in water (0.09% TFA). Yields are calculated from the starting resin 1.

21
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- 4 filtrate. This reduction has been observed in other on-resin borohydride chemistry
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- Alewood¹

22
- 84915375416
- 2 gas evolves. This process is repeated twice, to ensure complete reduction.

23
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- Acetogenic Isoquinoline Alkaloids, L. The Synthesis of All Possible Isomeric 6,8-Dioxygenated 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline Methyl Ethers – Useful Chiral Building Blocks for Naphthylisoquinoline Alkaloids
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.