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First Asymmetric Synthesis of (-)Methyl 2, 2-dimethyl-3-hydroxychromanyl-6-formate

XIE Zhi-xiang, HU Yang, LI Ying*   

  1. National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2003-11-12 Revised:2004-05-10 Online:2004-06-15 Published:2004-06-15
  • Contact: LI Ying*

Abstract: Aim To synthesize naturally occurring (-) methyl 2,2-dimethyl-3-hydroxychromanyl-6-formate. Methods Sharpless’ asymmetric dihydroxylation was employed to construct the 3-hydroxychroman. Results First asymmetric syn- thesis of (-) methyl 2, 2-dimethyl-3-hydroxychromanyl-6-formate (1) was accomplished starting from methyl 4-hydroxy- benzoate (2), and the absolute configuration was established. Conclusion A useful method for constructing chiral 3- hydroxychroman by employing Sharpless' asymmetric dihydroxylation is achieved.

Key words: 3-hydroxychroman, 3-hydroxychroman, Sharpless' asymmetric dihydroxylation, Sharpless' asymmetric dihydroxylation

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