Synthesis of C1-C8 and C9-C24 fragments of (-)-discodermolide: Use of asymmetric alkylation and stereoselective aldol reactions

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5449-5453

  Filla, Sandra A ^a   Song, Jinhua J ^a   Chen, Lihren ^a   Masamune, Satoru ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISCODERMOLIDE; NATURAL PRODUCT;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG ISOLATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033166757     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01009-6     Document Type: Article

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41. 6) δ 7.30 (d, J=9.0 Hz, 2H), 6.83 (d, J=9.0 Hz, 2H), 6.72 (dt, J=10.5, 16.8 Hz, 1H), 6.13 (t, J=10.8 Hz, 1H), 5.70 (t, J=10.5 Hz, 1H), 5.26 (dd, J=2.4, 17.1 Hz, 1H), 5.11 (d, J=10.2 Hz, 2H), 4.60 (d, J=10.5 Hz, 1H), 4.51 (d, J=10.2 Hz, 1H), 3.55-3.71 (m, 3H), 3.46 (dd, J=3.9, 6.6 Hz, 1H), 3.34 (dd, J=3.6, 6.9 Hz, 1H), 3.32 (s, 3H), 3.11 (m, 1H), 2.78 (m, 1H), 2.33 (t, J=12.9 Hz, 1H), 1.74-2.04 (m, 5H), 1.66 (s, 3H), 1.23 (d, J=6.6 Hz, 3H), 1.13 (d, J=7.1 Hz, 3H), 1.09 (d, buried, 3H), 1.08 (s, 9H), 1.02 (d, J=6.9 Hz, 3H), 1.00 (s, 9H), 0.95 (d, J=6.7 Hz, 3H), 0.20 (s, 3H), 0.18 (s, 3H), 0.11 (s, 3H), 0.09 (s, 3H).
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43. (b) Paterson, I.; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608.
44. 6) δ 4.24 (d, J=3.0 Hz, 1H), 3.89-4.05 (m, 2H), 3.60-3.69 (m, 2H), 3.46 (dd, J=4.5, 5.7 Hz, 1H), 3.27 (s, 3H), 1.94 (m, 1H), 1.58-1.80 (m, 3H), 1.03 (s, 9H), 0.99 (s, 9H), 0.90 (d, J=6.6 Hz, 6H), 0.18 (s, 3H), 0.13 (s, 3H), 0.07 (s, 3H), 0.02 (s, 3H).