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doi:10.1016/j.bmc.2005.02.005 
Copyright © 2005 Elsevier Ltd All rights reserved.
Novel A-ring analogs of the hormone 1
,25-dihydroxyvitamin D3: synthesis and preliminary biological evaluation
Gary H. Posnera, 
, 
, S.H. Tony Leea, Hyung Jin Kima, Sara Pelegb, Patrick Dolanc and Thomas W. Kenslerc
Received 16 December 2004;
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Abstract
Prepared from a commercial prostaglandin building block, novel vitamin D3 analogs with a contracted five-membered A-ring were designed and synthesized to mimic the A-ring diol structure of the natural hormone 1,25-dihydroxyvitamin D3. Prepared from commercial 1,4-cyclohexanedione, a structurally simplified analog was designed and synthesized in which a suitably oriented primary allylic hydroxyl group at the C-2 position might be a surrogate for the biologically important 1-OH in the natural hormone.
Keywords: Vitamin D analogs; SAR; Growth inhibition
Article Outline
- 1. Introduction
- 2. Results
- 3. Conclusion
- 4. Experimental
- 4.1. General methods
- 4.2. Ethyl 2-(4-tert-butylsiloxy-6-oxa-bicyclo[3.1.0]hexan-2-ylidene)acetate [(±)-6]
- 4.3. Ethyl 2-(3,4-bis(tert-butylsiloxy)cyclopentylidene)acetate [(±)-8]
- 4.4. 2-(3,4-Bis-(tert-butylsiloxy)cyclopentylidene)ethanol [(±)-9]
- 4.5. Phosphine oxide (±)-10
- 4.6. 1,3β(OH)2-2,19-nor D3 [(+)-2a] and 1β,3(OH)2-2,19-nor D3 [(+)-2b]
- 4.7. Bis-alcohols (E)-14a and (Z)-14b
- 4.8. Phosphine oxide 16
- 4.9. Vitamin D3 analog [(+)-3]
- Acknowledgements
- References
