TY - JOUR
T1 - Synthesis of 18,19-dihydroxycorticosterone
AU - Harnik, M.
AU - Carmely, S.
AU - Cojocaru, M.
AU - Kashman, Y.
PY - 1986
Y1 - 1986
N2 - A four-step synthesis of 18,19-dihydroxycorticosterone 5c, starting with 19,21-dihydroxy-3,20-dioxopregn-5-ene-18,11β-lactone-di-(ethylene ketal) 2, is presented. Reduction of 2 with sodium aluminum bis-(methoxyethoxy)hydride gave 11β,18,19,21-tetrahydroxy-pregn-5-ene-3,20-dione-di-(ethylene ketal) 3a. Acetylation furnished the corresponding 18,19,21-triacetate 3b, which on treatment with a mixture of perchloric and acetic acids gave 18,19-dihydroxycorticosterone 18,19,21-triacetate 4b. Mild saponification yielded the title compound which, on the basis of ir and nmr spectra, exists as one C-20 isomer of the hemiacetal structure 5c. Periodate oxidation of 5c gave the expected 11β,19-dihydroxy-3-oxoandrost-4-ene-17β,18-carbolatone 6b.
AB - A four-step synthesis of 18,19-dihydroxycorticosterone 5c, starting with 19,21-dihydroxy-3,20-dioxopregn-5-ene-18,11β-lactone-di-(ethylene ketal) 2, is presented. Reduction of 2 with sodium aluminum bis-(methoxyethoxy)hydride gave 11β,18,19,21-tetrahydroxy-pregn-5-ene-3,20-dione-di-(ethylene ketal) 3a. Acetylation furnished the corresponding 18,19,21-triacetate 3b, which on treatment with a mixture of perchloric and acetic acids gave 18,19-dihydroxycorticosterone 18,19,21-triacetate 4b. Mild saponification yielded the title compound which, on the basis of ir and nmr spectra, exists as one C-20 isomer of the hemiacetal structure 5c. Periodate oxidation of 5c gave the expected 11β,19-dihydroxy-3-oxoandrost-4-ene-17β,18-carbolatone 6b.
UR - http://www.scopus.com/inward/record.url?scp=0022870532&partnerID=8YFLogxK
U2 - 10.1016/0039-128X(86)90089-9
DO - 10.1016/0039-128X(86)90089-9
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AN - SCOPUS:0022870532
SN - 0039-128X
VL - 47
SP - 205
EP - 213
JO - Steroids
JF - Steroids
IS - 2-3
ER -