1987
DOI: 10.1021/jo00227a020
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Synthesis from pregnenolone of fluorescent cholesterol analog probes with conjugated unsaturation in the side chain

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Cited by 37 publications
(18 citation statements)
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“…2123 Despite reports of similar steroids undergoing Wittig condensation, 2428 all reaction conditions tested were unsuccessful. An approach involving vinyl Grignard addition to C-20 followed by oxidative rearrangement of the resulting tertiary alcohol was thus adopted (Supplementary data).…”
Section: Resultsmentioning
confidence: 99%
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“…2123 Despite reports of similar steroids undergoing Wittig condensation, 2428 all reaction conditions tested were unsuccessful. An approach involving vinyl Grignard addition to C-20 followed by oxidative rearrangement of the resulting tertiary alcohol was thus adopted (Supplementary data).…”
Section: Resultsmentioning
confidence: 99%
“…An approach involving vinyl Grignard addition to C-20 followed by oxidative rearrangement of the resulting tertiary alcohol was thus adopted (Supplementary data). 23,29 It was envisioned that aldehyde (20 E )- 15 would provide easy access to our desired sterols 2 – 10 via Wittig condensation and subsequent side-chain functionalization.…”
Section: Resultsmentioning
confidence: 99%
“…Following ap reviously reported procedure, [14] Grignarda ddition of vinyl magnesium bromideg ave am ixture (1:9) of the tertiary allylic alcohols 7a and 7b.T reatment of the mixture with pyridinium chlorchromate resulted in oxidative rearrangement of the allylic alcohol to yield an 80:20 E/Z mixture of b-substituted-a,b-unsaturated aldehydes, 8a and 8b. Notably,t he THP protectingg roup was chosen because it had previously resulted in am ore straightforwardc hromatographic separation of the 23(S)-and 23(R)-OHC stereoisomers.…”
Section: Resultsmentioning
confidence: 99%
“…Notably,t he THP protectingg roup was chosen because it had previously resulted in am ore straightforwardc hromatographic separation of the 23(S)-and 23(R)-OHC stereoisomers. Following ap reviously reported procedure, [14] Grignarda ddition of vinyl magnesium bromideg ave am ixture (1:9) of the tertiary allylic alcohols 7a and 7b.T reatment of the mixture with pyridinium chlorchromate resulted in oxidative rearrangement of the allylic alcohol to yield an 80:20 E/Z mixture of b-substituted-a,b-unsaturated aldehydes, 8a and 8b. Ak ey requiremento ft his synthetic route was the ability to reduce the a,b-unsaturation in 8a and/or 8b in as tereoselective fashion to provide both the R and S configurations of the C21 methyl moiety.I nitial attempts using standard palladium or platinum catalysts resultedi nn onselectiver eduction of the side chain olefin or complete saturation of the OHC scaffold ( Table 1, Entries 1-3).…”
Section: Resultsmentioning
confidence: 99%
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