Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate
Само за регистроване кориснике
1988
Чланак у часопису (Објављена верзија)
,
Elsevier
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The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.
Извор:
Tetrahedron, 1988, 44, 19, 6201-6206Финансирање / пројекти:
- Serbian Academy of Sciences and Arts
- Serbian Republic Research Fund
Институција/група
IHTMTY - JOUR AU - Mihailović, Milhailo Lj. AU - Lorenc, Ljubinka AU - Dabović, Milan AU - Bjelaković, Mira PY - 1988 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2699 AB - The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988. T2 - Tetrahedron T1 - Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate VL - 44 IS - 19 SP - 6201 EP - 6206 DO - 10.1016/S0040-4020(01)89810-0 ER -
@article{ author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Bjelaković, Mira", year = "1988", abstract = "The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.", journal = "Tetrahedron", title = "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate", volume = "44", number = "19", pages = "6201-6206", doi = "10.1016/S0040-4020(01)89810-0" }
Mihailović, M. Lj., Lorenc, L., Dabović, M.,& Bjelaković, M.. (1988). Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron, 44(19), 6201-6206. https://doi.org/10.1016/S0040-4020(01)89810-0
Mihailović ML, Lorenc L, Dabović M, Bjelaković M. Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron. 1988;44(19):6201-6206. doi:10.1016/S0040-4020(01)89810-0 .
Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Bjelaković, Mira, "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate" in Tetrahedron, 44, no. 19 (1988):6201-6206, https://doi.org/10.1016/S0040-4020(01)89810-0 . .