The first synthesis of herbicidin B. Stereoselective construction of the tricyclic undecose moiety by a conformational restriction strategy using steric repulsion between adjacent bulky silyl protecting groups on a pyranose ring

Journal of the American Chemical Society

Volumn 121, Issue 44, 1999, Pages 10270-10280

  Ichikawa, Satoshi ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HERBICIDIN B; NUCLEOSIDE ANALOG; SAMARIUM; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033544402     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992608h     Document Type: Article

References (49)

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33. 1H NMR analysis of the reaction mixture suggested that the hydrogenation product was a mixture of anomers, and the α-anomer readily isomerized during the workup to give the β-anomer as the sole product.
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35. Molecular modeling of both herbicidin B (1b) and its 6′-epimer 23 was carried out using Macromodel (version 4.5) software. Preferred conformations were determined from the results of Monte Carlo conformer searches starting from previously minimized structures of the two compounds. Minimization employed the MM2* force field. Sets of conformers close to minimum were found for 1b and 23, respectively. The minimum-energy conformation for 23 was consistent with that suggested from the coupling constants and NOE relationships of 23. The minimum-energy conformer of 6′-epi-herbicidin B (23) was approximately 3.0 kcal/mol more stable than that of herbicidin B.
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44. Remaining starting material 29a was observed on TLC.
45. The stereochemistries of the two diastereomers were not confirmed.
46. 3SnH were tried.
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48. 1H NMR spectrum of the crude reduction product suggested that it was an anomeric mixture (α/β = 3/1).
49. A byproduct, the structure of which has not been determined, was also obtained in the hydrogenation of 31a, and it made the yield of 32a low. On the other hand, production of such a byproduct was not observed in the hydrogenation of 31c.