Enantioselective Synthesis of (2R, 4'R, 8'R)-. ALPHA.-Tocopherol (Vitamin E) Based on Enzymatic Function.

M Nozawa, K Takahashi, K Kato, H Akita

Index: Nozawa, Masako; Takahashi, Keiko; Kato, Keisuke; Akita, Hiroyuki Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 2 p. 272 - 277

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Citation Number: 19

Abstract

Syntheses of (S)-chroman-2-carboxaldehyde congener 1 and (S)-chiral isoprene unit 3 were achieved based on the enzymatic acetylation of (±)-chroman-2-methanol 6 and (±)-(2, 3)- anti-2-methyl-3-(p-methoxyphenyl)-1, 3-propane diol 12, respectively. Synthesis of the side- chain part corresponding to (3R, 7R)-3, 7, 11-trimethyldodecan-1-ol 27 was achieved by the couping reaction of (S)-3 and (R)-3, 7-dimethyloctyl iodide 4. The Witting reaction of (3R, ...