Structurally simplified zaragozic acid (squalestatin): Stereoselective preparation of a 3,4-unsubstituted derivative

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9009-9012

  Ito, Hisanaka ^a,c   Matsumoto, Miyoko ^a   Yoshizawa, Takeshi ^a   Takao, Ken Ichi ^b   Kobayashi, Susumu ^b  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SQUALENE SYNTHASE; SQUALESTATIN; ZARAGOZIC ACID A;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030823093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10407-5     Document Type: Article

References (22)

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18. 1H-NMR (400 or 200 MHz) and IR spectra, and satisfactory high-resolution MS was obtained for them.
19. 2=CHMgBr with ketone 16 prepared from D-xylose was also examined to form 17 with high diastereoselectivity (>95 : 5). The sense of the diastereofacial selection was found to be opposite to the case of 5. Since 17 has the wrong stereochemistry for the synthesis of the core moiety, it could not be utilized for synthetic purpose. formula presented.
20. 4-NMO was also examined for the preparation of 4-hydroxy derivative in mind, but the dihydroxylation proceeded very slowly to afford an almost 1:1 diastereomeric mixture.
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22. 7 474.2615, found 474.2613.