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Volumn , Issue 5, 2009, Pages 0803-0807

Simple synthesis of conjugated all-(E)-polyenic aldehydes, ketones, and esters using chemoselective cross-metathesis and an iterative sequence of reactions: Application to the synthesis of navenone B

(3) Bouzbouz, Samir a Roche, Christophe a Cossy, Janine a

a CNRS (France)

Author keywords

Allylation; Cross metathesis; Elimination; Navenone B; Polyenes

Indexed keywords

EID: 62449169795 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087953 Document Type: Article

Times cited : (18)

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- Synthesis of Compound 4 To a solution of alkene 3 (190 mg, 0.45 mmol) in CH2Cl2 (2.3 mL) was added at r.t. ethyl acrylate (0.15 mL, 1.35 mmol) and Ru-II (14 mg, 0.023 mmol, The reaction mixture was stirred at r.t. overnight and then concentrated in vacuo. Purification of the residue by flash chromatography (hexane/EtOAc, 99:1) afforded 4 (154 mg, 69, as a yellow oil. Rf, 0.43 (hexane/EtOAc, 9:1, IR: 1739, 1720, 1656, 1232 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.66 (m, 4 H, 7.41 (m, 6 H, 6.83 (dt, J, 15.8, 7.2 Hz, 1 H, 5.85 (dt, J, 15.8, 1.5 Hz, 1 H, 5.76 (m, 1 H, 5.47 (dt, J, 15.5, 6.8 Hz, 1 H, 5.34 (m, 1 H, 4.18 (q, J, 6.8 Hz, 2 H, 3.69 (t, J, 6.4 Hz, 2 H, 2.49 (m, 2 H, 2.28 (q, J, 6.8 Hz, 2 H, 2.02 (s, 3 H, 1.26 (t, J, 6.8 Hz, 3 H, 1.04 (s, 9 H, 13C NMR 75 MHz, CDCl3, δ, 170.1
- 3): δ = 170.1, 166.2, 143.3, 135.6, 133.8, 131.6, 129.6, 129.1, 127.6, 124.2, 72.8, 63.1, 60.3, 37.3, 35.6, 26.8, 21.2, 19.2, 14.2. MS: m/z = 377, 241, 199, 105.

38
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- 3): δ = 7.66 (m, 4 H), 7.41 (m, 6 H), 7.30 (dd, J = 15.5, 11.5 Hz, 1 H), 6.44 (dd, J = 15.1, 10.2 Hz, 1 H), 6.13 (dd, J = 15.1, 11.5 Hz, 1 H), 6.09 (dd, J = 14.8, 10.2 Hz, 1 H), 5.92 (dt, J = 14.8, 6.4 Hz, 1 H), 5.85 (d, J = 15.5 Hz, 1 H), 4.13 (q, J = 7.2 Hz, 2 H), 3.69 (t, J = 6.4 Hz, 2 H)
- 3): δ = 167.2, 144.7, 140.9, 136.6, 135.6, 133.8, 131.6, 129.6, 128.2, 127.6, 120.3, 63.2, 60.2, 36.3, 26.8, 19.2, 14.3. MS: m/z = 377, 227, 199, 105.

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