Highly stereoselective synthesis of trans-trans-4-aryl-2,3-oxetanedimethanols: Preparation of oxetanocin A analogues

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7667-7670

  Jung, Michael E ^a   Nichols, Christopher J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXETANOCIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030597162     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01720-0     Document Type: Article

References (31)

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28. 3, 400 MHz) δ: 1.57 (d, J = 6.1 Hz), 1.48 (d, J = 6.1 Hz), 1.46 (d, J = 6.5 Hz), 1.33 (d, J = 6.5 Hz) in a ratio of 2 : 10 : 1.5 : 1.
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30. 30. Slightly different reaction conditions produce a different mixture of the products 13 and 14, in which more of the cyclic compound is formed.
31. 31. Proton NMR data: 7a: 7.40 (5H, m); 6.12 (1H, ddd, J = 17.1, 10.4, 7.9 Hz), 5.36 (1H, d, J = 7.2 Hz), 5.23 (1H, dt, J = 17.1, 1.2 Hz), 5.20 (1H, ddd, J = 10.4, 1.3, 0.8 Hz), 4.70 (1H, ddd, J = 8.0, 6.9, 6.0 Hz), 3.47 (1H, dd, J = 9.8, 5.9 Hz), 3.39 (1H, dd, J = 9.8, 8.0 Hz), 3.09 (1H, qt, J = 7.3, 1.0 Hz). 8a: 7.28-7.37 (5H, m); 5.83 (1H, ddd, J = 17.3, 10.4, 8.6 Hz), 5.45 (1H, dddd, J = 5.3, 4.4, 1.6, 0.5 Hz), 5.14 (1H, ddd, J = 10.4, 1.6, 0.6 Hz), 4.97 (1H, ddd, J = 17.3, 1.6, 0.9 Hz), 4.84 (1H, d, J = 10.0 Hz), 4.41 (1H, ddd, J = 10.6, 4.4, 0.2 Hz), 4.00 (1H, dd, J = 10.6, 1.6 Hz), 2.78 (1H, b td, J = 9.3, 5.3 Hz), 2.14 (3H, s). 14: 7.24 (2H, m), 6.86 (2H, m), 5.93 (1H, ddd, J = 17.5, 10.5, 8.1 Hz), 5.26 (1H, ddd, J = 10.5, 1.6, 0.7 Hz), 5.11 (1H, dt, J = 17.5, 1.3 Hz), 4.85 (1H, d, J = 10.0 Hz), 4.48 (1H, m), 4.33 (1H, dd, J = 9.9, 4.2 Hz), 3.98 (1H, dd, J = 9.9, 1.5 Hz), 3.80 (3H, s). 2.69 (1H, b td, J = 9.0, 4.8 Hz), 1.78 (1H, d, J = 3.2 Hz).