4.7 Review

Pd(0)-Catalyzed-Mediated Synthesis of Vitamin D Compounds

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ADVANCED SYNTHESIS & CATALYSIS
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WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202301201

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Vitamin D; Synthesis; Pd(0)-catalyzed cyclizations; Pd(0)-catalyzed couplings; A-Ring synthons; Heck-Suzuki/Miyaura-Negishi-Sonogashira-Stille

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1α,25-dihydroxyvitamin D3 (1,25D3), the active form of vitamin D3, plays a crucial role in regulating mineral homeostasis, cell growth, and immune responses. However, its clinical applications are limited due to hypercalcemic effects. Therefore, there has been a focus on synthesizing highly active and non-calcemic analogs of 1,25D3 for the treatment of hyperproliferative diseases.
1 alpha,25-Dihydroxyvitamin D3 (1,25D3), the hormonally active form of vitamin D3, regulates mineral homeostasis, cell growth, cell differentiation-proliferation, apoptosis, and immune responses. 1,25D3 activates more than 229 genes associated with several diseases, including arthritis, diabetes and cancer, suggesting its implications in a broader range of biological functions than originally thought. Despite the wide range of biological activities, the clinical applications of 1,25D3 have been limited due to its collateral hypercalcemic effects. This problem has boosted intense synthetic activity in the vitamin D area in the last decades aimed at the development of highly active and non-calcemic analogs for treatment of hyperproliferative diseases. This review covers the most useful synthetic approaches to 1,25D3 analogs containing the natural vitamin D triene system with emphasis on the Pd(0)-catalyzed transformations involved in the formation of the vitamin D triene system and A-ring synthons. image

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