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Synthesis of an analogue of squalamine: 6β-hydroxyl-3-aminosterol†
Feng Cai,
Wei-Shan Zhou,
Feng Cai
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorWei-Shan Zhou
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorFeng Cai,
Wei-Shan Zhou,
Feng Cai
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorWei-Shan Zhou
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this author†
Dedicated to Professor Chengye Yuan on the occasion of his 80th birthday.
Abstract
6,β-Hydroxylsqualamine was synthesized stereoselectively in 13 steps and 19% overall yield from methyl hyodeoxycholanate by using stereospecific epoxidation and asymmetric isopropylation as key steps.
References
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- 11 Compound 16: 1H NMR (CD3OD, 300 MHz) δ: 0.79 (s, 3H), 0.91–1–.00 (m. 9H), 1.10 (s, 3H), 1.12–1–.35 (m, 8H), 1.35–1–.50 (m, 6H), 1.50–1–.70 (m, 4H), 1.70–2–.10 (m, 13H), 2.10–2–.30 (m, 2H), 3.03 (t, J=6.0 Hz, 2H), 3.12 (t, J=6.0 Hz, 2H), 3.16–3–.29 (m, 6H), 3.81 (br, 1H); 13C NMR (CD3OD, 75 MHz) δ: 11.2, 14.7, 16.6, 17.8, 18.0, 20.7, 23.9, 25.6, 25.7, 26.0, 27.9, 29.6, 30.0, 30.2, 31.9, 33.5, 35.3, 35.6, 38.1, 39.2, 39.4, 39.9, 42.4, 43.6, 46.6, 47.5, 48.1, 54.0, 56.2, 56.3, 57.4, 70.7, 76.3; MS (ESI) m/z: 548[M+l]+; HRMS calcd for C34H66N3O2 (M + H) 548.5150, found 548.5161.
- 12 Compound 2a: 1H NMR (CD3OD, 300 MHz) δ: 0.79 (s, 3H), 0.97–1–.03 (m, 9H), 1.11 (s, 3H), 1.12–1–.35 (m, 7H), 1.30–1–.75 (m, 10H), 1.70–1–.90 (m, 11H), 1.95–2–.18 (m, 5H), 3.03 (t, J=6.0 Hz, 2H), 3.10 (t 2H, J=6.0 Hz), 3.20–3–.29 (m, 5H), 3.84 (br, 1H), 4.10–4–.18 (m, 1H); 13C NMR (CD3OD, 75 MHz) δ: 84.9, 70.4, 62.0, 57.9, 56.2, 54.0, 50.9, 48.5, 46.8, 44.8, 42.6, 41.7, 40.0, 39.3, 38.6, 38.0, 36.0, 35.4, 31.3, 30.7, 30.3, 28.7, 27.8, 24.6, 24.3, 23.8, 23.2, 23.1, 18.0, 17.0, 16.8, 14.6, 11.2; MS (ESI) m/z: 628 [(M+1]+; HRMS calcd for C34H66N3O5S (M + H) 628.4718, found 628.4702.