Rearrangement reaction of tetrahydrofurans and tetrahydropyrans having a C1'-mesyloxy group on the C2-side chain with zinc acetate

Heterocycles

Volumn 50, Issue 2, 1999, Pages 919-928

  Nagasawa, Kazuo ^a   Hori, Nobuyuki ^a   Koshino, Hiroyuki ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN; TETRAHYDROPYRAN DERIVATIVE; ZINC ACETATE;

ACETYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033117665     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)92     Document Type: Article

References (8)

1. For a review, see: Y. Shimizu, Chem. Rev., 1993, 93, 1685.
2. (a) T. Nakata, S. Nomura, and H. Matsukura, Tetrahedron Lett., 1996, 37, 233.
3. (b) T. Nakata, S. Nomura, and H. Matsukura, Chem. Pharm. Bull., 1996, 44, 627.
4. (c) K. Nagasawa, N. Hori, R. Shiba, and T. Nakata, Heterocycles, 1997, 44, 105.
5. Only one enantiomer of the racemate was drawn for the sake of simplicity.
6. K. Ishihara, H. Kurihara, and H. Yamamoto, J. Org. Chem., 1993, 58, 3791.
7. The ratio (x%) of the conformer (11b) having the axial C2-H was calculated as the coupling constants of 2,3-diaxial and 2,3-diequatorial protons on tetrahydropyran ring are 12 and 2 Hz, respectively; [12x + 2(100-x)]/100=8.1. x=61%.
8. C. Dalvit and G. Bovermann, Magn. Reson. Chem., 1995, 33, 156.