Total syntheses of natural pseurotins A and F2 and azaspirene

Heterocycles

Volumn 62, Issue , 2004, Pages 161-166

  Aoki, Shin Ya ^a   Oi, Takahiro ^a   Shimizu, Kazuya ^a   Shiraki, Ryota ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 OXA 7 AZASPIRO[4.4]NON 2 ENE 4,6 DIONE; AZASPIRENE; GLUCOSE; PSEUROTIN A; PSEUROTIN F2; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; OXYGENATION; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0345828942     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s(p)25     Document Type: Article

References (32)

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25. 2O) m/z 399.1318, found 399.1318.
26. 3OH) m/ z 399.1318, found 399.1318.
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30. We also explored the following conditions. After treating 6 with 1.0 molar equiv. of KHMDS, 5.0 molar equiv. of the dienal (12) was added with 5.0 molar of chlorotriethylsilane (TESCl)19a,b in THF or THF/PhMe(1:1, v/v) at -78 °C. Under these conditions, the silylenol ether derived from 6 was only an obtainable product, whose geometrical stereochemistry was not determined.
31. We believe that the TES group in 14 migrated to the tertiary hydroxy group in the oxidation step. To suppress the formation of 16, we examined a variety of oxidation conditions. However, the ratio of 15 to 16 was approximately 2:1 in all cases.
32. +) m/z 369.1576, found 369.1572.