Qinghui Wang1, Zongtao Lin1, Tae-Kang Kim2, Andrzej T Slominski3, Duane D Miller1, Wei Li4. 1. Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, Memphis, TN 38163, United States. 2. Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, United States; Department of Pathology, University of Alabama at Birmingham, Birmingham, AL 35294, United States. 3. Department of Dermatology, University of Alabama at Birmingham, Birmingham, AL 35294, United States; Department of Pathology, University of Alabama at Birmingham, Birmingham, AL 35294, United States; Veteran Affairs Medical Center, Birmingham, AL 35294, United States. 4. Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, Memphis, TN 38163, United States. Electronic address: wli@uthsc.edu.
Abstract
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.
A total synthetic strategy of 20S-hydroxyvitamin D3 [n class="Chemical">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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