A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7887-7890

  Hatakeyama, Susumi ^a   Yoshida, Masashi ^a   Esumi, Tomoyuki ^a   Iwabuchi, Yoshiharu ^a   Irie, Hiroshi ^a   Kawamoto, Toshiki ^b   Yamada, Hidetoshi ^b   Nishizawa, Mugio ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SERINE; THERMOZYMOCIDIN; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030778622     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10077-6     Document Type: Article

References (30)

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25. 2, an 1:1 mixture of 12 and 13 was obtained in 81% yield.
26. 1H NMR). Significant NOEs were observed between the olefinic methine proton and the proton of CH bearing the benzyloxy group and between the methylene protons of the hydroxymethyl group and the methine proton of the oxazole ring.
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28. Birch reduction without saponification caused also reduction of the methyl ester.
29. 3) δ 211.7 (s), 172.4 (s), 170.2 (s), 169.5 (s), 169.0 (s), 135.1 (d), 123.2 (d), 81.5 (d), 72.0 (d), 62.8 (t), 62.6 (s), 42.9 (t), 42.8 (t), 32.5 (t), 32.2 (t), 31.6 (t), 29.1 (t), 29.0 (t), 29.0 (t), 28.9 (t), 23.9 (t), 23.8 (t), 22.8 (q), 22.5 (t), 20.6 (q), 20.4 (q), 14.1 (q).
30. 3OD) δ 214.4 (s), 173.4 (s), 134.7 (d), 126.8 (d), 73.7 (d), 71.3 (s), 70.4 (d), 65.1 (t), 43.5 (t), 43.5 (t), 38.7 (t), 33.7 (t), 32.8 (t), 30.4 (t), 30.2 (t), 30.1 (t), 30.0 (t), 24.9 (t), 23.6 (t), 14.4 (q).