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Total synthesis of biologically active 20S-hydroxyvitamin D3.

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.

SUBMITTER: Wang Q

PROVIDER: S-EPMC4659745 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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Total synthesis of biologically active 20S-hydroxyvitamin D3.

Wang Qinghui Q Lin Zongtao Z Kim Tae-Kang TK Slominski Andrzej T AT Miller Duane D DD Li Wei W

Steroids 20151001

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 proliferat ...[more]

PMID: 26433048

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