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Synlett

Volumn , Issue 8, 2008, Pages 1216-1218

A convergent total synthesis of (+)-febrifugine

(4) Sieng, Bora a Ventura, Oscar Lozano a Bellosta, Véronique a Cossy, Janine a

a CNRS (France)

Author keywords

Allyltitanation; Antimalarial activity; Febrifugine; Total synthesis; Wittig reaction

Indexed keywords

FEBRIFUGINE;

ANTIMALARIAL ACTIVITY; ARTICLE; DICHROA FEBRIFUGA; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; PROTON NUCLEAR MAGNETIC RESONANCE; WITTIG REACTION;

EID: 44349114951 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072736 Document Type: Article

Times cited : (20)

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- A better yield was observed for the oxidative cleavage of the double bond when performed in two separated steps.

31
- 44349142104
- The yield for 14 corresponds to the isolated yield but the protection did not reach completion (71% conversion).
- The yield for 14 corresponds to the isolated yield but the protection did not reach completion (71% conversion).

32
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- A cross-metathesis reaction using methyl vinyl ketone and the protected allylic alcohol 15, in the presence of the Grubbs-Hoveyda catalyst failed.

33
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- Compound 17: [α]D25-22.1 (c 1.17, CHCl3, IR (neat, 2979, 1678, 1612, 1365, 1118, 1028, 775, 734, 697 cm-1. 1H NMR (400 MHz, CDCl3, δ, 8.29 (dd, J, 8.0, 1.5 Hz, 1 H, 7.90 (s, 1 H, 7.80-7.73 (m, 2 H, 7.51 (ddd, J, 8.0, 6.8, 1.6 Hz, 1 H, 6.94 (dd, J, 16.0, 5.8 Hz, 1 H, 6.46 (dd, J, 16.0, 1.3 Hz, 1 H, 4.99 (d, J, 1.6 Hz, 2 H, 4.65 (dABsyst, J, 6.9 Hz, 1 H, 4.63 (dABsyst, J, 6.9 Hz, 1 H, 4.30, m, 1 H, 3.61 (br t, J, 6.8 Hz, 2 H, 3.39 (s, 3 H, 1.76-1.60 (m, 4 H, 1.51 (s, 18 H, 13C NMR (100 MHz, CDCl3, δ, 191.0 (s, 160.9 (s, 152.8 (2 s, 148.6 (d, 148.2 (s, 146.4 (d, 134.4 (d, 127.6 (d, 127.4 (d, 126.8 (d, 126.3 (d, 121.9 (s, 95.1 (t, 82.3 (2s, 75.2 (q, 55.8 (d, 52.6 (t, 45.9 (t, 31.8 (t, 28.1 (6 q, 24.6 t
- 3): δ = 191.0 (s), 160.9 (s), 152.8 (2 s), 148.6 (d), 148.2 (s), 146.4 (d), 134.4 (d), 127.6 (d), 127.4 (d), 126.8 (d), 126.3 (d), 121.9 (s), 95.1 (t), 82.3 (2s), 75.2 (q), 55.8 (d), 52.6 (t), 45.9 (t), 31.8 (t), 28.1 (6 q), 24.6 (t).

34
- 44349122712
- Efficient isomerization of isofebrifugine into febrifugine by heating in water has been reported by Takeuchi et al, see ref. 8d
- Efficient isomerization of isofebrifugine into febrifugine by heating in water has been reported by Takeuchi et al., see ref. 8d.

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