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C.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ol052680mb00017\/ol052680mb00017_1","volume-title":"Dictionary of Terpenoids","volume":"1","author":"The","year":"1991"},{"volume":"0","volume-title":"The flask was fitted with a condenser and refluxed for 6 h. The reaction mixture was then reduced","author":"The 0.","key":"ol052680mb00018\/ol052680mb00018_1"},{"key":"ol052680mb00020\/ol052680mb00020_1","unstructured":"Breitmaier, E.; Voelter, W.Carbon-13 NMR Spectroscopy.High-Resolution Methods and Applications in Organic Chemistry andBiochemistry; VCH:\u2009 New York, 1987; pp 192\u2212195."},{"volume-title":"B. Chem. Commun.","year":"2004","author":"The","key":"ol052680mb00021\/ol052680mb00021_1"},{"key":"ol052680mb00022\/ol052680mb00022_1","doi-asserted-by":"crossref","first-page":"678","DOI":"10.1002\/hlca.200390067","volume":"86","author":"Fr\u00e1ter G.","year":"2003","journal-title":"Helv. Chim. Acta"},{"key":"ol052680mb00023\/ol052680mb00023_1","unstructured":"The following procedure was used to prepare compound9:\u2009 To a solution of [RhCl(PPh3)3] (95 mg, 0.10 mmol) and PPh3(370 mg, 1.4 mmol) in THF at rt were sequentially addedi-PrOH (8.8 mL, 1.4 mmol) and 570 mg, (1.3 mmol) of the corresponding aldehyde in 8 mL of THF. The mixture was stirred for 10 min to dissolve the catalyst, treated with TMSCHN2(0.90 mL, 1.8 mmol, 2.0 M solution in Et2O), and stirred at rt during 45 min. The reaction mixture was diluted with water and extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to yield 220 mg (39%) of9as a red oil:\u2009 [\u03b1]22D= +140.6 (c0.34, CHCl3); IR (film) \u03bdmax3085, 2929, 2868, 2844, 1673, 1452, 1380, 1066 cm-1;1H NMR (CDCl3, 300 MHz) \u03b4 6.34 (dd,J= 17.5, 10.7 Hz, 1H), 5.35 (d,J= 17.5 Hz, 1H), 5.13 (d,J= 10.7 Hz, 1H), 4.75 (br s, 1H), 4.72 (br s, 2H), 4.44 (br s, 1H), 4.41 (br s, 2H), 4.34 (br s, 2H), 4.23 (br s, 2H), 2.83 (dd,J= 16.7, 9.4 Hz, 1H), 2.67 (dd,J= 16.7, 3.4 Hz, 1H), 2.61 (br d,J= 9.4 Hz, 1H), 2.39 (ddd,J= 11.4, 3.7, 2.3 Hz, 1H), 2.14 (td,J= 12.9, 5.6 Hz, 1H), 1.75 (m, 1H), 1.65\u22121.10 (m, 7H), 0.90 (s, 3H), 0.83 (s, 3H), 0.76 (s, 3H);13C NMR (CDCl3, 75 MHz) \u03b4 199.4, 149.2, 141.7, 136.6, 135.9, 128.3, 126.3, 116.5, 106.4, 55.3, 51.5, 41.9, 39.2, 39.0, 37.5, 34.2, 33.6, 33.5, 23.9, 21.7, 19.3, 14.8; MS (EI)m\/z(relative intensity) 444 [M+] (100), 426 (2), 411 (3), 254 (6), 239 (35), 211 (21), 153 (5), 121 (6), 91 (12). Anal. Calcd for C28H36FeO:\u2009 C, 75.67; H, 8.16. Found:\u2009 C, 75.73; H, 8.10."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol052680m","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,9,23]],"date-time":"2021-09-23T13:32:46Z","timestamp":1632403966000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol052680m"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,1,19]]},"references-count":30,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2006,2,1]]}},"alternative-id":["10.1021\/ol052680m"],"URL":"https:\/\/doi.org\/10.1021\/ol052680m","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"type":"print","value":"1523-7060"},{"type":"electronic","value":"1523-7052"}],"subject":[],"published":{"date-parts":[[2006,1,19]]}}}