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Tetrahedron Letters

Volumn 36, Issue 19, 1995, Pages 3425-3428

A synthetic approach towards octalactin A, based on the stereoselective reduction of α,β-unsaturated ketones

(4) Bach, Jordi a Berenguer, Ramon a Garcia, Jordi a Vilarrasa, Jaume a

a UNIVERSITY OF BARCELONA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; OCTALACTIN A; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0028965619 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(95)00498-2 Document Type: Article

Times cited : (42)

References (23)

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3
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7
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- 2. Several attempts of direct transformation of 6 into 3a by addition of organolithium or Grignard reagents failed.

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11
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12
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13
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- CBS reagent: (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole (Corey, E.J.; Shibata, S.; Bakshi, R.K. J. Org. Chem. 1988, 53, 2861 and ref. therein); in a similar reduction carried out at low temperature with catecholborane instead of borane, lower yield and selectivity were observed (58%, 86% e.e.);

14
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- Noyori¹ Tomino² Yamada³ Nishizawa⁴

15
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16
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17
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18
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- D.e. of the alcohol was determined by HPLC analysis of the Mosher ester. The absolute configuration was established by the Kakisawa method (Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092) and confirmed by comparison of the allylic alcohol derived from Sharpless' epoxidation of a mixture of epimers.

19
- 84914025412
- 2 group, before hydroboration) were unsuccessful.

20
- 84914025411
- Compounds 13 and 14 could be separated by column chromatography. The mixture were analysed by HPLC of the Mosher diester. The relative configuration of both compounds were determined by NMR analysis of the p-methoxybenzylidene acetal derivatives.

21
- 84914025410
- A similar directed epoxidation is reported in Buszek's approach (ref. 2). However, in this case the hydroxylic substrate was not obtained in a stereoselective manner, but rather as a mixture of epimers differing in configuration at C9. By contrast, in the Clardy synthesis (ref. 3), the introduction of the epoxide group has been reported to occur in a 2:1 diastereomeric ratio by nucleophilic epoxidation on (+)-Octalactin B.

22
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23
- 84914025409
- Protected (S)-3-hydroxy-4-methylpentanal was synthesised by ozonolysis of O-silylated (S)-2-methylhex-5-en-3-ol (95% e.e.) obtained by asymmetric allylboration of isobutyraldehyde (Racherla, U.S.; Brown, H.C. J. Org. Chem. 1991, 56, 401).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.