A novel approach to prostaglandins from the corey lactone involving BF3-mediated reactions of a sulphone and aldehydes

Achmatowicz, Barbara; Baranowska, E.; Daniewski, A. R.; Pankowski, J.; Wicha, J.

doi:10.1016/s0040-4039(01)80897-2

Cited by 29 publications

(5 citation statements)

References 16 publications

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“…For instance, varying the nature of the counter ion can efficiently shift this unfavorable equilibrium. Thus, replacing lithium by magnesium [30][31][32][33][34][35][36][37] or the use of a lithiated sulfone/boron trifluoride combination [38][39][40][41][42][43] have proved to be effective. In Scheme 3.11, reaction 3.11 shows the beneficial use of magnesium salts in the Julia coupling employed as a key step in the synthesis of 24-epi-26,26,26,27,27,27- Furthermore, trapping of the in situ generated alkoxide -usually with Ac 2 O, BzCl, MsCl or TMSCl -can be a method of choice to shift the equilibrium in favor of the desired addition product.…”

Section: Preparation Of 12-disubstituted Olefinsmentioning

confidence: 99%

The Julia Reaction

Dumeunier

Markó

2003

Modern Carbonyl Olefination

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Section: Preparation Of 12-disubstituted Olefinsmentioning

confidence: 99%

The Julia Reaction

Dumeunier

Markó

2003

Modern Carbonyl Olefination

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“…23 Sometimes, the modification step of the hydroxy group is omitted and b-hydroxy sulfones 140 are subjected to reductive elimination. 102 Thus the reduction of the adduct 142 with sodium amalgam gives the alkene 143 in high yield.…”

Section: A the Julia Reactionmentioning

confidence: 99%

“…1, 2, 99 ± 101 Subsequent addition of the anion 138 to the carbonyl group yields a mixture of diastereomeric b-hydroxy sulfones 140. The reaction is accelerated in the presence of Lewis acids, such as boron trifluoride etherate 102 and magnesium bromide. 103 Then, the hydroxy group of b-hydroxy sulfones 140 is converted into a good leaving group (acetate, benzoate, p-toluenesulfonate); subsequent reduction of a-acyloxy sulfones 141 with sodium amalgam in methanol gives alkenes.…”

Section: A the Julia Reactionmentioning

confidence: 99%

Olefination of carbonyl compounds: modern and classical methods

Korotchenko¹,

Nenajdenko²,

Баленкова³

et al. 2004

Russ. Chem. Rev.

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The published data on the methods for alkene synthesis The published data on the methods for alkene synthesis by olefination of carbonyl compounds are generalised and sys-by olefination of carbonyl compounds are generalised and systematised. The main attention is given to the use of transition tematised. The main attention is given to the use of transition metals and organoelement compounds. The review covers the metals and organoelement compounds. The review covers the data on both classical and newly developed methods that are little data on both classical and newly developed methods that are little known to chemists at large. The bibliography includes 276 known to chemists at large. The bibliography includes 276 references references. .

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“…Recentlyl, we have used the Julia olefination2 to provide a convenient synthesis of prostaglandins. The key intermediate (1) in the route to PGF2, (2a) was obtained by BF3-mediated addition of the sulphone (3) and a 2-hydroxyheptanal derivative, followed by the reductive removal of the benzenesulphinyl and the neighbouring hydroxy (acyloxy) groups. The advantage of the use of an optically active 2-hydroxy aldehyde is in the introduction of a 'pre-formed' chiral centre into the prostaglandin chain.'…”

mentioning

confidence: 99%