1990
DOI: 10.1021/jo00300a001
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Asymmetric total synthesis of an A-ring precursor to hormonally active 1.alpha.,25-dihydroxyvitamin D3

Abstract: A new sulfinyl orthoester has been designed and used effectively in one-flask syntheses of dienoate esters from allylic alcohols; this new method as well as a highly stereocontrolled [2 + 4]-cycloaddition are applied to synthesis of la,25-dihydroxyvitamin D3.The Diels-Alder reaction certainly is one of the very best methods for controlling stereochemistry while forming two carbon-carbon bonds in one operation.1 23Attempts to use 2-pyrones and to isolate the initial Diels-Alder cycloadducts have regularly been … Show more

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Cited by 81 publications
(30 citation statements)
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“…A complementary approach as shown in Scheme was also reported later by Posner [32b]. Diels‐Alder reaction of enantiomerically pure 2‐pyrone ( S )‐lactate 112 and benzyl vinyl 113 ether promoted by Lewis acidic NMR shift reagent (–)‐Pr(hfc) 3 provided bicyclic lactone 114 in 98% yield in 98: 2 dr. Methanolysis of lactone 114 followed by the decarboxylation and double bond migration by N ‐methylmorpholine under high pressure produced cyclohexenol benzyl ether 116 .…”
Section: Natural Product Total Syntheses Via Diels‐ Alder Reaction Ofmentioning
confidence: 83%
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“…A complementary approach as shown in Scheme was also reported later by Posner [32b]. Diels‐Alder reaction of enantiomerically pure 2‐pyrone ( S )‐lactate 112 and benzyl vinyl 113 ether promoted by Lewis acidic NMR shift reagent (–)‐Pr(hfc) 3 provided bicyclic lactone 114 in 98% yield in 98: 2 dr. Methanolysis of lactone 114 followed by the decarboxylation and double bond migration by N ‐methylmorpholine under high pressure produced cyclohexenol benzyl ether 116 .…”
Section: Natural Product Total Syntheses Via Diels‐ Alder Reaction Ofmentioning
confidence: 83%
“…These findings encouraged Posner and his coworkers to apply the Diels‐Alder reaction of 2‐pyrone in the efficient preparations of calcitirol and its analogs …”
Section: Natural Product Total Syntheses Via Diels‐ Alder Reaction Ofmentioning
confidence: 93%
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“…As a key step in the total synthesis of an A-ring precursor 45 to 1α,25-dihydroxyvitamin D 3 , an inverse-electron-demand Diels-Alder reaction was catalysed by MAD 1 to promote cycloaddition between pyrone sulfone 42 and the vinyl ether (S)-43 (Scheme 11) [18].…”
Section: Scheme 10mentioning
confidence: 99%