- 1α-Hydroxyvitamin D5, its synthesis and use in cancer prevention
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A compound of formula I: wherein R1 is hydrogen, R2 is —CH3, R3 is —CH3, and R4 is hydrogen, useful in cancer prevention and therapy.
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Page/Page column Sheet 2; 4
(2010/02/11)
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- Synthesis of 1α-Hydroxyvitamin D5 using a modified two wavelength photolysis for vitamin D formation
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1α-Hydroxyvitamin D5 (1) is a promising chemopreventive agent for breast cancer and is being developed as a drug. We report a synthesis for this vitamin D analogue which uses a photochemical method for the B-ring opening, leading to the conjugated triene system. The precursor 7-dehydrositosteryl acetate (4) obtained through a one-pot, five-step procedure, was completely free of the 4,6-diene isomer that usually forms in the 5,7-diene synthesis. The pre-vitamin isomer (11) was generated using a modified two-wavelength photolysis procedure that increases the yield for this step more than 3-fold compared to classically used photolysis. The 1α-hydroxylation step was performed on the 3-triethylsilyl-trans-vitamin D5 (17) obtained via the sulfur dioxide adduct of cis-vitamin D5, in an overall yield of 48%. Photoisomerization and deprotection completed the synthesis.
- Moriarty, Robert M.,Albinescu, Dragos
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p. 7624 - 7628
(2007/10/03)
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