An expedited approach to the vitamin D trans-hydrindane building block from the Hajos dione.
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: see text]
Chochrek
Paweł
P
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw 42, Poland.
Wicha
Jerzy
J
D002117:Calcitriol / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D007192:Indenes; D002117:Calcitriol