SCOPUS 정보 검색 플랫폼

Tetrahedron Letters

Volumn 25, Issue 9, 1984, Pages 923-926

The regiospecific total synthesis of lavendamycin methyl ester

(2) Kende, Andrew S a Ebetino, Frank H a

a UNIVERSITY OF ROCHESTER (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; LAVENDAMYCIN METHYL ESTER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0021338389 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)80063-0 Document Type: Article

Times cited : (66)

References (20)

1
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- Gould¹ Weinreb²

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- Cheng¹ Yan²

7
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- 8-Hydroxyquinaldic acid
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- Irving¹ Pennington²

8
- 0009684426
- This mp is of the less polar diastereomer of 12 obtained by chromatography of the mixture on Si gel (10% EtOAC/hexanes). Cyclization to 13a was done on the mixture.
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 2217
- Snyder¹ Matteson²

9
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- Kanaoka¹ Sato² Ban³

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- Pratt¹

11
- 0017086958
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- Lown¹ Sim²

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- 3 in aqueous THF followed by dithionite reduction. C.H. Tann (personal communication).
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- Parker¹ Sworin²

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- 37049169525
- 177. The reactions of metallic salts of acidss with halogens. Part II. The interaction of silver trifluoroacetate or silver perchlorate and halogens in various solvents
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- Hazeldine¹ Sharpe²

14
- 84918414493
- 3): δ12.00 (bs,1H),9.156(d,1H,J=9.1),9.07(d,1H, J-9.1),8.61(s,1H),8.37(d,1H,J=8.0),7.67(m,2H),7.41(t,1H),4.36(s,3H),4.10(s,3H),3.22(s,3H).

15
- 84918414492
- 3): δ 12.44(bs,1H),8.86(d,1H,J=8.8),8.39(d,1H,J=7.9),8.28(d,1H,J=8.9),7.73(d,1H, J=7.8),7.65 t,1H,7.39(t,1H),6,99(bs,3H),4.23(s,3H),4.09(s,3H),3.23(s,3H).

16
- 84918414491
- 3): δ 11.84(bs,1H),9.05(d,1H,J=8.4),8.46(d,1H, J=8.4),8.34,(d,1H,J=8.0),7.79(d,1H,J=8.2),7.66(t,1H),7.59(s,1H),7.40(t,1H),4.09(s,3H),3.20(s,1H). For a related synthesis of simple 7-haloquinoline-5,8-quinones see
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- Petrow¹ Sturgeon²

17
- 84918414490
- 2) to give 4b.

18
- 84918414489
- 2 (0.34), EtOAc-MeOH-HOAc in 92.5-6.5-1.5 ratio (0.80). The UV spectra of natural and synthetic 4b were identical.

19
- 84918414488
- 3).

20
- 84918414487
- 1H-NMR and tlc, but further studies are required to achieve a preparative conversion.

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