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Tetrahedron Letters

Volumn 36, Issue 23, 1995, Pages 4089-4092

Total synthesis of D-(+)-showdomycin from syn-2,5-disubstituted tetrahydrofuran

(2) Kang, Sung Ho a Lee, Sung Bae a

a Korea Advanced Institute of Science and Technology (KAIST) (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

SHOWDOMYCIN;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

STREPTOMYCES SHOWDOENSIS;

EID: 0029068837 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(95)00722-O Document Type: Article

Times cited : (14)

References (21)

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- Kang¹ Lee²

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4
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5
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6
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- Nakagawa¹ Kano² Tsukuda³ Koyama⁴

7
- 0141535686
- THE STRUCTURE OF SHOWDOMYCIN, A NOVEL CARBON-LINKED NUCLEOSIDE ANTIBIOTIC RELATED TO URIDINE
- (1967) Proceedings of the National Academy of Sciences , vol.57 , pp. 548-553
- Darnall¹ Townsend² Robins³

8
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- Daves¹ Cheng²

9
- 0025290279
- and references cited therein
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 891-892
- Barton¹ Ramesh²

10
- 84914018778
- (S)-1,2,4-Butanetriol was purchased from Aldrich Chemical Co.

11
- 0001462758
- (1971) Tetrahedron , vol.27 , pp. 1973-1996
- Achmatowicz¹ Bukowski² Szechner³ Zwierzchowska⁴ Zamojski⁵

12
- 0344512526
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- Jurczak¹ Pikul²

13
- 84914018777
- The acetonide group was partially hydrolyzed.

14
- 84914018776
- After protection of the hydroxyl groups in 4 as acetonide, the acetonide was treated with bromine in aqueous THF to give bislactols, which could be oxidized to monolactone but not to anhydride under various oxidation reaction conditions.

15
- 0014799112
- (1970) Tetrahedron Lett. , vol.11 , pp. 2297-2300
- Kalvoda¹ Farkas² Sorm³

16
- 37049094299
- C-nucleoside studies. Part 7. A new synthesis of showdomycin, 2-?-D-ribofuranosylmaleimide
- (1979) Journal of the Chemical Society, Perkin Transactions 1 , pp. 225-227
- Buchanan¹ Edgar² Power³ Shanks⁴

17
- 0022633765
- 2O with 0.5% dioxane): δ 62.11, 67.30 (dioxane as reference), 71.58, 75.20, 78.23, 84.01, 129.94, 147.83, 173.18, 173.79 ppm
- (1986) J. Org. Chem. , vol.51 , pp. 495-503
- Barrett¹ Broughton²

18
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- The conversion of furanyl derivatives into pyrroles could not be realized using ethyl azidoformate: see
- (1964) Tetrahedron Lett. , vol.5 , pp. 2185-2190
- Hafner¹ Kaiser²

19
- 84914018775
- The major isomer of 13 has the same furanyl structure as in 6.

20
- 84914018774
- All new compounds showed satisfactory spectral data.

21
- 84914018773
- Although diol 15 could be converted into D-(+)-showdomycin 1, the overall chemical yield of 1 was 15 ∼ 25% from 4.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.