2002
DOI: 10.1021/jo025987x
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Catalytic Enantioselective Synthesis of (−)-Prostaglandin E1 Methyl Ester Based on a Tandem 1,4-Addition−Aldol Reaction

Abstract: Catalytic enantioselective 1,4-additions and tandem 1,4-addition-aldol reactions of dialkylzinc reagents to cyclopentene-3,5-dione monoacetals in the presence of an in situ generated Cu(OTf)(2)/chiral phosphoramidite catalyst result in highly functionalized cyclopentane building blocks with ee's up to 97%. A new synthesis of cyclopentene-3,5-dione monoacetals is presented as well as its use in a tandem 1,4-addition-aldol protocol for the catalytic asymmetric total synthesis of (-)-PGE(1) methyl ester. This syn… Show more

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Cited by 102 publications
(39 citation statements)
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“…Monodentate phosphoramidites 4 ± 13 [26,27] with a BINOL backbone ( Table 2, entries 1 ± 10) afforded 2a/ 3a in yields that were generally, although not always, good. The C À C bond formation was always in favor of the S N 2' product, with regioselectivities up to 94 : 6; although the enantioselectivities obtained by applying these ligands were highly varying.…”
Section: Resultsmentioning
confidence: 99%
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“…Monodentate phosphoramidites 4 ± 13 [26,27] with a BINOL backbone ( Table 2, entries 1 ± 10) afforded 2a/ 3a in yields that were generally, although not always, good. The C À C bond formation was always in favor of the S N 2' product, with regioselectivities up to 94 : 6; although the enantioselectivities obtained by applying these ligands were highly varying.…”
Section: Resultsmentioning
confidence: 99%
“…A few other monodentate ligands 14 ± 18 [27,28] with N,N-bis(1-phenylethyl)amine attached to different backbones were subsequently screened ( Table 2, entries 11 ± 15). The three ligands with a BINOL-type backbone gave similar results to the former ligands.…”
Section: Resultsmentioning
confidence: 99%
“…We achieved on improvement in product yield in the synthesis of (AE)-coronafacic acid by examination of the synthetic route. For example, exoselectivity in the Diels-Alder reaction was improved to endo:exo > 1:25 by the use of 6 as substrate, 17) and the yields in the subsequent reductions were also improved by the use of 8 or ,-unsaturated ketone (9) as intermediate. Fortunately, the reduction of 9 in toluene proceeded with high stereoselectivity to give (S)-10 as a single product.…”
Section: Resultsmentioning
confidence: 99%
“…A mixture of (þ)-5 and its diastereomer (20.5 mg) was separated by HPLC on a triacontyl column (Develosil RPAQUEOUS, 20 Â 250 mm, Nomura Chemical, Nagoya) with 56% aqueous CH 3 OH containing 30 mM HCO 2 NH 4 at 8. FITC-labeled coronatine (17). To a solution of (þ)-5 (1.10 mg, 3.05 mmol), FITC-alkyne 16 (2.40 mg, 3.25 mmol), and sodium ascorbate (643 mg, 3.25 mmol) in EtOH (330 ml) and 1 M aqueous NaHCO 3 (330 ml) was added CuSO 4 (104 mg, 0.652 mmol).…”
Section: Methodsmentioning
confidence: 99%
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