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Volumn , Issue 11, 2009, Pages 1730-1732

Thieme chemistry journal awardees - Where are they now? Synthesis of (-)-cubebol by intramolecular cyclopropanation of a terminal epoxide

Author keywords

Cubebol; Epoxide; Intramolecular cyclopropanation; Lithium 2,2,6,6 tetramethylpiperidide; Total synthesis

Indexed keywords

CUBEBOL; CYCLOPROPANE DERIVATIVE; EPOXIDE; MENTHONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOPROPANATION; LITHIATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 67649958241 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217353 Document Type: Article

Times cited : (8)

References (21)

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17
- 67649992265
- Characterisation Data for (3R,6S)-6-Isopropyl-3-methyl-2- methylenecyclohexanol (12, α]D 25 -100.9 (c, 1.42, CHCl3, IR: 3480 (br, 3067 (w, 2958 (s, 2933 (s, 2870 (m, 1644 (w, 1475 (w, 1450 (w, 1029 (m, 948 (m, 905 (s) cm-1. 1H NMR (400 MHz, CDCl3, δ, 5.02 (d, J, 1.0 Hz, 1 H, CH2, 4.73 (d, J, 1.5 Hz, 1 H, CH2, 3.83 (br s, 1 H, CHOH, 2.20-2.29 (m, 1 H, CHMe2, 1.94-2.03 (m, 1 H, CHMe, 1.79-1.84 (m, 1 H, H-4a, 1.62-1.71 (m, 1 H, H-5a, 1.56 (d, J, 5.5, 1 H, OH, 1.17-1.29 (m, 2 H, H-5b, H-6, 1.09 (d, J, 6.5 Hz, 3 H, CHMe, 0.95-1.02 (m, 1 H, H-4b, 0.93 (d, J, 7.0 Hz, 3 H, Me of CHMe2, 0.87 (d, J, 7.0 Hz, 3 H, Me of CHMe 2, 13C NMR (100 MHz, CDCl3, δ, 156.9, C, 100.6, CH2, 74.3 (COH, 51.9 (C-6, 36.7 CHMe, 35
- 19: 151.1487; found: 151.1488.

18
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19
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20
- 67649979749
- 1R,4R,5R,6R,7S,10R, 7-Isopropyl-10-methyltricyclo-[4.4.0.01,5]decan-4-ol (15, n-BuLi (1.6 M in hexanes, 3.75 mL, 6.0 mmol) was added to a stirred solution of 2,2,6,6-tetramethylpiperidine (1.0 mL, 6.0 mmol) in t-BuOMe (30 mL) at -78 °C. The resulting pale yellow solution of LTMP was stirred at r.t. for 15 min and then cooled to 0 °C in an icebath. To a stirred solution of epoxide 6 (593 mg, 2.85 mmol) in t-BuOMe (14 mL) at 0 °C was added the above LTMP solution dropwise via a cannula over 3 h. The reaction mixture was stirred at r.t. for 17 h, then MeOH (3 mL) was added, the mixture was evaporated under reduced pressure and the residue dry-loaded onto a small amount of SiO2 and purified by column chromatography (SiO 2, gradient elution, 20-35% Et2O-PE) to give a white solid, cyclopropyl alcohol 15 (534 mg, 90, Rf 0.4 40% Et
- 23: 191.1800; found: 191.1811.

21
- 67649970455
- Characterisation data for (1S,4S,5S,6S, 7S,10R)-7-Isopropyl-10-methyltricyclo[4.4.0.01,5]decan- 4-ol (17, α]D 25 +28.0 (c, 1.0, CHCl3, IR: 3310 (br, 2954 (s, 2971 (s, 1470 (m, 1443 (w, 1383 (w, 1327 (w, 1057 (w, 974 (s) cm-1, 1H NMR (400 MHz, CDCl3, δ, 4.21 (d, J, 5.0 Hz, 1 H, CHOH, 1.95-2.03 (m, 1 H, H-2a, 1.88-1.94 (m, 1 H, H-10, 1.69-1.72 (m, 1 H, H-3a, 1.46-1.62 (m, 3 H, H-7, H-8a, H-9a, 1.32-1.43 (m, 3 H, CHMe2, H-2b, H-3b, 1.08 (d, J, 7.0 Hz, 3 H, CHMe, 1.01 (d, J, 3.5 Hz, 1 H, H-5, 0.92 (d, J, 6.5 Hz, 3 H, Me of CHMe2, 0.89 (d, J, 6.5 Hz, 3 H, Me of CHMe2, 0.86-0.88 (m, 1 H, H-9b, 0.71-0.84 (m, 1 H, H-8b, 0.68 (t, J, 4.2, 1 H, H-6, 13C NMR (100 MHz, CDCl3, δ, 75.6 (C-4, 40.3 C
- 23: 191.1800; found: 191.1806.

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