A strategy for exploiting the pseudosymmetry of the C1-C13 stretch of discodermolide

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1413-1416

  Parker, Kathlyn A ^a   Katsoulis, Ioannis A ^a,b  

^a STONY BROOK UNIVERSITY   (United States)

^b BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DISCODERMOLIDE;

ARTICLE; CHEMICAL STRUCTURE; MODEL; SYNTHESIS;

ALKANES; CARBAMATES; LACTONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRONES; STEREOISOMERISM;

EID: 2442507882     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049735p     Document Type: Article

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42. On the basis of enantiomeric and diastereomeric ratios reported by McDonald for epoxidation of a similar enynol prepared from the (R)-CBS reagent, we expected Sharpless oxidation of our alcohol (S)-14 (93% of the CBS product) with the reagent from D-(-)-diisopropyl tartrate to provide a mixture of and epoxy alcohol 16 and its syn diastereomer in a ratio close to 99:1. We expected these conditions to convert (R)-14, 7% of the CBS product, to a 1:1 mixture of the syn epoxy alcohol and the enantiomer of 16. See: McDonald, F. E.; Reddy, K. S.; Diaz, Y. J. Am. Chem. Soc. 2000, 722, 4304-4309 and Supporting Information.
43. 1H NMR spectrum of epoxy alcohol 13 exhibited signals at 5.45 (t, J= 10.3 Hz, 1H), 5.18 (t, J = 10.3 Hz, 1H), 4.65 (d, J = 8.3 Hz, 1 H). In the same region, its syn diastereomer showed 5.42 (t, J = 10.5 Hz, 1H), 5.36 (t, J = 10.5 Hz, 1H), 4.26 (bs, 1H).
44. 1H NMR spectrum of the (R)-Mosher ester of 13 (from the (S)-Mosher acid chloride) exhibited clear signals at 5.82 (dd, J = 9.5, 4.2 Hz, 1H), 5.57 (t, J = 10.5 Hz, 1H), 5.15 (t, J = 10.3 Hz, 1H). This pattern was resolved from and easily distinguished from that of the (S)-Mosher ester of 13: 5.79 (dd, J = 9.8, 4.8 Hz, 1H), 5.57 (dd, J = 10.7, 9.8 Hz, 1H), 5.27 (t, J = 10.7 Hz, 1H).
45. The and epoxy alcohol 13 was contaminated with a small amount of an impurity that appeared to contain a trans olefin.
46. Full details of structure assignment and characterization of anti diol 7 are contained in Supporting Information.