A new access to the 6,8-dioxabicyclo[3.2.1]octane ring system using a three-component reaction: Enantioselective synthesis of (+)-iso- exo -brevicomin

Synlett

Volumn , Issue 2, 2010, Pages 207-210

  Bouziane, Asmae ^a   Régnier, Thomas ^a   Carreaux, François ^a   Carboni, Bertrand ^a   Bruneau, Christian ^a   Renaud, Jean Luc ^b  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b 6 Bd du Maréchal Juin   (France)

Author keywords

Asymmetric catalysis; Boron; Cycloaddition; Natural product; Redox isomerization

Indexed keywords

6,8 DIOXABICYCLO[3.2.1]OCTANE; BREVICOMIN; OCTANE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; ENANTIOSELECTIVITY; ISOMERIZATION;

EID: 75649098638     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218561     Document Type: Article

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40. General Procedure and Selected Characterization Data To a stirred solution of 3 (0.3 mmol) in CH2Cl2 (3 mL) at 0 C was added BF3OEt2 (0.33 mmol). After 10 min, the resulting solution was warmed to r.t. and stirred for 90 min (excepted in the case of 3d). The reaction mixture was quenched with sat. aq NaHCO3 (1 mL), and the aqueous phase was extracted with Et2O (2 ×2 mL). The combined organic phases were washed with brine, dried over MgSO4, filtrated, and concentrated under reduced pressure. Compounds 4 were purified by flash chromatography on silica gel (210400 mesh). Compound 4d was obtained as a colorless oil (95%). [a]D 25 +33.5 (c 1.75, CH2Cl2). 1H NMR (300 MHz, CDCl3): d = 1.03 (s, 9 H), 1.911.97 (m, 1 H), 2.332.42 (m, 1 H), 4.26 (d, 1 H, J = 8.4 Hz), 4.44 (d, 1 H, J = 8.8 Hz), 4.47 (d, 1 H, J = 4.9 Hz), 5.505.52 (m, 1 H), 5.605.63 (m, 1 H), 5.986.04 (m, 1 H), 7.207.28 (m, 7 H), 7.357.49 (m, 6 H), 7.667.71 (m, 2 H). 13C NMR (75 MHz, CDCl3): d = 19.4, 26.9, 33.8, 72.0, 75.0, 88.7, 100.9, 124.3, 127.4, 127.5, 127.6, 127.7, 128.0, 128.9, 129.7, 129.8, 133.0, 134.0, 135.9, 136.0, 141.4. Anal. Calcd for C29H32O3Si: C, 76.28; H, 7.06. Found: C, 76.35; H, 7.01.
41. The ee was measured by GC analysis using a chiral stationary phase (Varian WCOT Fused Silica 25 0.25 mm coated CP Chirasil-dex CB DF = 0.25).
42. The ee was measured by GC analysis using a chiral stationary phase (Varian WCOT Fused Silica 25 ×0.25 mm coated CP Chirasil-dex CB DF = 0.25).
43. 1-Phenylpropan-1-one can be obtained from the corresponding allylic alcohol in 97% yield with only 2 mol% of [RuCp(MeCN)3][PF6] in toluene at r.t. These new conditions represent an improvement of the previously described process with this catalyst.
44. Characterization Data for Key Synthetic Intermediates Compound 3e was obtained from 1 in 70% yield as a colorless oil. [a]D25+72 (c 0.59, CH2Cl2). 1H NMR (300 MHz, CDCl3): d = 1.181.25 (m, 6 H), 2.192.22 (m, 2 H), 2.72 (br s, 1 H), 3.53 (dq, 1 H, J = 7.1, 9.3 Hz), 3.693.72 (m, 1 H), 3.96 (dq, 1 H, J = 7.1, 9.3 Hz), 3.984.03 (m, 1 H), 4.72 (dd, 1 H, J = 4.8, 6.1 Hz), 5.605.63 (m, 1 H), 5.785.80 (m, 1 H). 13C NMR (75 MHz, CDCl3): d = 15.2, 18.6, 31.1, 64.4, 69.6, 78.8, 98.5, 124.9, 126.1. HRMS (EI): m/z [MOCH2CH3]+ calcd for C7H11O2: 127.0759; found: 127.0755. Compound 12 was obtained as colorless oil (mixture of diastereomers, 63%). 1H NMR (300 MHz, CDCl3): d = 1.20 (d, 3 H, J = 5.9 Hz), 1.351.70 (m, 6 H), 1.81 (br s, 1 H), 2.68 (br s, 1 H), 3.403.43 (m, 2 H), 4.094.12 (m, 1 H), 4.43 (d, 1 H, J = 11.5 Hz), 4.68 (d, 1 H, J = 11.5 Hz), 5.11 (dd, 1 H, J = 1.2, 10.4 Hz), 5.23 (d, 1 H, J = 17.2 Hz), 5.88 (ddd, 1 H, J = 6.2, 10.4, 17.2 Hz), 7.267.43 (m, 5 H). 13C NMR (75 MHz, CDCl3): d = 15.5, 21.3, 21.4, 32.5, 32.6, 36.9, 71.0, 73.0, 73.1, 74.8, 74.9, 78.3, 78.4, 114.5, 114.6, 127.7, 127.8, 128.5, 138.3, 141.1, 141.2. ESI-HRMS: m/z [M + Na]+ calcd for C16H24O3Na: 287.1623; found: 287.1623. (+)-Iso-exo-brevicomin was obtained as a colorless oil (highly volatile, 60%): [a]D25 +53 (c 0.3, CHCl3); lit.14d [a]D+54 (c 0.5, CHCl3). 1H NMR (300 MHz, CDCl3): d = 0.96 (t, 3 H, J = 7.9 Hz), 1.18 (d, 3 H, J = 6.5 Hz), 1.431.95 (m, 8 H), 4.06 (br s, 1 H), 4.22 (q, 1 H, J = 6.5 Hz). 13C NMR (75 MHz, CDCl3): d = 7.3, 17.1, 21.6, 28.0, 30.6, 33.5, 75.5, 79.9, 109.5. Anal. Calcd for C9H16O2: C, 69.19; H, 10.32. Found: C, 69.27; H, 10.41.