An expedited approach to the vitamin D trans-hydrindane building block from the Hajos dione.

@article{Chochrek2006AnEA,
  title={An expedited approach to the vitamin D trans-hydrindane building block from the Hajos dione.},
  author={Paweł Chochrek and Jerzy Wicha},
  journal={Organic letters},
  year={2006},
  volume={8 12},
  pages={2551-3}
}
Efficient and operationally simple synthesis of the key trans-hydrindane alcohol building block for the synthesis of calicitriol (1alpha,25-dihydroxyvitamin D(3)) has been developed. Epoxy alcohol prepared almost quantitatively from the Hajos dione was reduced at the quaternary carbon by the Hutchins procedure (NaBH(3)CN-BF(3).Et(2)O). The diol was selectively deoxygenized either using the Barton-McCombie reaction (with Bu(3)SnH-AIBN) or via the respective iodohydrine (with LiAlH(4)). [reaction… CONTINUE READING

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