Synthesis of palau'amide and its diastereomers: confirmation of its stereostructure

Tetrahedron Letters

Volumn 50, Issue 52, 2009, Pages 7343-7345

  Sugiyama, Hirokazu ^a   Watanabe, Atsushi ^a   Teruya, Toshiaki ^a   Suenaga, Kiyotake ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEPSIPEPTIDE; PALAU AMIDE; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; LYNGBYA; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 70449129814     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.059     Document Type: Article

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13. 3) (major rotamer) δ 7.50-7.16 (m, 5H), 6.54 (t, J = 7.6 Hz, 1H), 5.33 (m, 2H), 5.10 (dd, J = 3.4, 6.8 Hz, 1H), 4.94 (m, 1H), 4.20 (m, 1H), 4.12 (dd, J = 7.6, 7.6 Hz, 1H), 3.76-3.47 (m, 3H), 3.22 (s, 3H), 3.20-2.79 (m, 2H), 3.09 (s, 3H), 2.61 (s, 3H), 2.33 (dd, J = 7.6, 7.6 Hz, 2H), 2.21 (dt, J = 4.0, 8.0 Hz, 2H), 2.05-1.94 (m, 2H), 1.78 (s, 3H), 1.66-1.07 (m, 13H), 1.37 (d, J = 7.6 Hz, 3H), 0.99-0.78 (m, 15H). Signals due to three protons (NH × 2, OH) were not observed. The ratio of rotamers was ca. 15:1.