SCOPUS 정보 검색 플랫폼

Prostaglandins

Volumn 18, Issue 5, 1979, Pages 737-743

Letter to the editor Synthesis of 16-fluoromethylene-prostaglandin F2α

(3) Kosuge, S a Nakai, H a Kurono, M a

a ONO PHARMACEUTICAL CO (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

16 FLUOROMETHYLENEPROSTAGLANDIN F2ALPHA; 16-FLUOROMETHYLENEPROSTAGLANDIN F2ALPHA; PROSTAGLANDIN F;

ANIMAL; ARTICLE; CHEMISTRY; DIARRHEA; DRUG EFFECT; FEMALE; IATROGENIC DISEASE; MOUSE; RAT; SYNTHESIS; UTERUS CONTRACTION; 16 FLUOROMETHYLENEPROSTAGLANDIN F2 ALPHA; ANIMAL EXPERIMENT; DRUG SYNTHESIS; FEMALE GENITAL SYSTEM; METHODOLOGY;

ANIMAL; CHEMISTRY; DIARRHEA; FEMALE; MICE; PROSTAGLANDINS F, SYNTHETIC; RATS; UTERINE CONTRACTION;

EID: 0018539005 PISSN: 00906980 EISSN: None Source Type: Journal
DOI: 10.1016/0090-6980(79)90094-7 Document Type: Letter

Times cited : (11)

References (12)

1
- 84970587033
- TOTAL SYNTHESIS OF 14-FLUOROPROSTAGLANDIN F2α AND 14-FLUOROPROSTACYCLIN
- and references cited therein
- (1978) Chemistry Letters , pp. 1001
- Grieco¹ Yokoyama² Nicolaou³ Smith⁴ Ogletree⁵ Lefer⁶

2
- 84912326411
- SYNTHESIS OF 16,16-(2-FLUOROTRIMETHYLENE)-PROSTAGLANDINS AND 16,16-(2,2-DIFLUOROTRIMETHYLENE)-PROSTAGLANDINS
- (1979) Chemistry Letters , pp. 63
- Nakai¹ Hamanaka² Kurono³

3
- 33748632765
- (1961) Tetrahedron Lett. , pp. 43
- Shen¹ Lucas² Sarett³

4
- 84912324062
- In the absence of KF, heating of 4(at 150°C for 1 h) gave the decarboxylated product 11 in good yield. Further treatment of 11 with KF(10 equiv) in DME at 40°C for 20 h gave no desired compound 5(11 was recovered).

5
- 84912324061
- We tentatively assigned the stereochemistry of 5 to E configuration based on the following considerations. Formula A must be the most favourable conformer of 4 based on the dipole-dipole interaction between C-F and C-COO. By decarboxylative elimination reaction of 4, E-isomer 5 should be obtained via the most favourable transition state from conformer A

6
- 84912324060
- ppm(2H, quart, J=7.0 Hz)].

7
- 84912324059
- Because the compound 6b was inert to the next condensation reaction, the mixture of 6a and 6b was used without further separation.

8
- 0015238075
- (1971) J. Amer. Chem. Soc. , vol.93 , pp. 1491
- Corey¹ Albonico² Koelliker³ Schaaf⁴ Varma⁵

9
- 84912324058
- The compound 9 was very sensitive to an acid. In the presence of a mineral and/or organic acid, the compound 9 was easily changed into 12.

10
- 84912324057
- The epimeric mixture of 1 and 2 was also very sensitive to an acid. In the presence of an acid, the mixture of 1 and 2 was easily converted into 13.

11
- 0014514052
- By analogy to the TLC behaviour natural and 15-epi prostaglandins, the more polar isomer has been assigned the natural configuration
- (1969) J. Lipid Res. , vol.10 , pp. 316
- Andersen¹

12
- 84912324056
- 2 methyl ester.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.