[The stereocontrolled synthesis of 1-acetylenyl-3-tert-butyldiphenylsilyloxy-exo-bicyclo [3. 1. 0] hexane].
OBJECTIVE
In order to find out more effective method for the synthesis of the A-ring synthon, (-)-1-acetylenyl-3-tert-butyldiphenylsily-loxy-exo-bicyclo [3. 1. 0] hexane (3), for 19-nor-1 alpha, 25-dihydroxyvitamin D3(2)with commercial value.


METHODS
We synthesized the A-ring synthon (+/-)(3) via nine steps with good yield starting from 3-cyclopentenyl alcohol(4).


RESULTS
The spectral data of compound (+/-)(3) is the same as the spectral data of (-)(3) which reported preciously by us.


CONCLUSIONS
The method is an effective method for synthesis of the A-ring synthon (3).
Wu
Y
Y
Department of Medicinal Chemistry, School of Pharmacy, WCUMS, Chengdu 610041, China.
Guan
M
M
Zhu
H
H
D000480:Alkynes; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D004872:Ergocalciferols / Q000138:chemical synthesis*; D012833:Siloxanes / Q000138:chemical synthesis*
C475004:1-acetylenyl-3-tert-butyldiphenylsilyloxy-exo-bicyclo(3.1.0)hexane; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D004872:Ergocalciferols; D012833:Siloxanes; C084656:paricalcitol