SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 18, 2007, Pages 2894-2896

A concise synthesis of (-)-deoxoprosopinine

(2) Pandey, Satyendra Kumar a Kumar, Pradeep a

a NATIONAL CHEMICAL LABORATORY (India)

Author keywords

Hydroboration oxidation; Jacobsen's HKR; Piperidine alkaloids; Sharpless AD; Total synthesis

Indexed keywords

DEOXOPROSOPININE; EPOXIDE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DIHYDROXYLATION; HYDROBORATION; HYDROLYSIS KINETICS; OXIDATION; SHARPLESS EPOXIDATION;

EID: 36549068138 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991056 Document Type: Article

Times cited : (22)

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- The diastereoselectivity was determined from 1H NMR and 13C NMR spectral data. Spectral data of compound 11: mp 137°C; [α]D25 +6.90 (c 1.00, CHCl 3, IR (CHCl3, ν, 3434, 3018, 2927, 1719, 1508, 1216 cm-1. 1H NMR (200 MHz, CDCl3, δ, 0.89 (t, J, 5.95 Hz, 3 H, 1.26-1.70 (m, 29 H, 2.27 (br s, 2 H, 3.62-3.71 (m, 1 H, 3.91 (d, J, 6.45 Hz, 1 H, 4.06 (d, J, 1.61 Hz, 1 H, 4.29 (q, J, 6.72, 13.70 Hz, 2 H, 4.55 (d, J, 8.87 Hz, 1 H, 5.10 (s, 2 H, 7.32-7.38 (m, 5 H) ppm. 13C NMR (50 MHz, CDCl 3, δ, 14.0, 22.6, 25.8, 29.2, 29.6, 29.8, 31.4, 31.8, 35.5, 51.1, 61.8, 66.4, 72.3, 73.4, 127.9, 128.4, 136.5, 156.2, 173.4 ppm. ESI-MS: m/z, 516 [M, Na, Anal. Calcd, ) for C28H 47NO6: C, 68.12; H, 9.60; N, 2.84. Found: C, 68.17; H, 9.58; N, 2
- 6: C, 68.12; H, 9.60; N, 2.84. Found: C, 68.17; H, 9.58; N, 2.82.

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43
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- Spectral data of compound 13: mp 96°C; [α]D 25 +5.65 (c 0.60, CHCl3, IR (CHCl3, ν, 3583, 3436, 3019, 2928, 1725, 1519, 1455, 1215 cm-1. 1H NMR (200 MHz, CDCl3, δ, 0.88 (t, J, 6.07 Hz, 3 H, 1.26-1.79 (m, 30 H, 2.11 (br s, 1 H, 2.65-2.74 (m, 1 H, 3.58 (d, J, 4.06 Hz, 1 H, 4.11-4.17 (m, 1 H) 4.21 (q, J, 7.12, 13.86 Hz, 2 H) ppm. 13C NMR (50 MHz, CDCl3, δ, 14.0, 14.2, 22.6, 26.1, 28.0, 29.3, 29.5, 29.6, 31.8, 35.8, 51.6, 60.8, 61.5, 65.5, 172.2 ppm. ESI-MS: m/z, 342 [M, H, Anal. Calcd, ) for C20H39NO3: C, 70.33; H, 11.51; N, 4.10. Found: C, 70.35; H, 11.48; N, 4.12
- 3: C, 70.33; H, 11.51; N, 4.10. Found: C, 70.35; H, 11.48; N, 4.12.

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