Synthetic studies on the seven- and eight-membered rings by the intramolecular Nozaki-Hiyama reaction of the allylic phosphates

Tetrahedron Letters

Volumn 45, Issue 47, 2004, Pages 8653-8657

  Iwamoto, Mitsuhiro ^a   Miyano, Masayuki ^a   Utsugi, Masayuki ^a   Kawada, Hatsuo ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Allylic phosphate; Carbocyclic ring; Intramolecular reaction; Nozaki Hiyama reaction; Seven and eight membered ring

Indexed keywords

ALLYL COMPOUND; PACLITAXEL; PHOSPHATE;

ALLYLATION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NOZAKI HIYAMA REACTION; STRUCTURE ANALYSIS;

EID: 7044231370     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.142     Document Type: Article

References (34)

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24. 3
25. Prolonged reaction time (3 days) did not improve the yield of 17 (14%, with formation of 16 (45%))
26. Preparation of the chloride 15 from 12 was attempted, but the yield was very low; hence, 14 was prepared through a different route
27. Relative configuration was elucidated by NOE experiment
28. 2O. The result of this experiment showed no incorporation of deuterium into the product; hence, the formed allylic chromium was surmised to react with water existing somewhere in the reaction mixture to afford 16
29. Now we are studying the ring-enlargement reaction of the seven-membered rings in 18 and 20 to the eight-membered rings to construct the 6-8-6 ring system required for the synthesis of Taxol™
30. 2, 82% (two steps). Allylic phosphates 23, 25, and 27 were synthesized similarly
31. By-products were shown below. The intermolecular reaction was neglected even under diluted conditions (0.002 M)
32. Configuration of 26 shown in Scheme 6 is that of the major diastereomer
33. By-products possessing similar structure to 32 and 33 were obtained in 12% each
34. Compound 29 was prepared according to the method in Ref. 5