| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 2027712 | Steroids | 2015 | 10 Pages |
•Key intermediates 7 and 12 were generated in parallel via modified synthetic ways.•Simultaneous removal of EOM and TBS was completed using camphorsulfonic acid.•20S-Hydroxyvitamin D3 was synthesized in 16 steps with an overall yield of 0.4%.•Synthetic 20S-(OH)D3 activated VDR and initiated expression of downstream genes.•20S-(OH)D3 was potent in inhibition of melanoma cells proliferation.
A total synthetic strategy of 20S-hydroxyvitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig–Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.
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