2003
DOI: 10.1021/ol035752n
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Abstract: [reaction: see text] The chemoselectivity of the ruthenium-catalyzed hydrative diyne cylization is explored in an expeditious synthesis of the tricyclic alkaloids cylindricine C, D, and E.

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Cited by 109 publications
(55 citation statements)
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“…40 2, 3) also take longer reaction duration. Table 1 Screening of other selenating reagents for the synthesis of 2c 45 The milder condition, shorter reaction duration (20 min) and the 50 excellent yield obtained in case of 2c prompted us to examine the scope and generality of the present protocol for the conversion of a series of N-protected amino alkyl iodides 1 to the corresponding diselenides 2 ( Table 2). The present methodology is an efficient one due to the following attributes: compatibility with the 55 common urethane protecting groups like Boc/Cbz/Fmoc, starting material can be prepared easily, monoselenides and triselenides are not formed as byproducts, simple workup and purification procedure.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…40 2, 3) also take longer reaction duration. Table 1 Screening of other selenating reagents for the synthesis of 2c 45 The milder condition, shorter reaction duration (20 min) and the 50 excellent yield obtained in case of 2c prompted us to examine the scope and generality of the present protocol for the conversion of a series of N-protected amino alkyl iodides 1 to the corresponding diselenides 2 ( Table 2). The present methodology is an efficient one due to the following attributes: compatibility with the 55 common urethane protecting groups like Boc/Cbz/Fmoc, starting material can be prepared easily, monoselenides and triselenides are not formed as byproducts, simple workup and purification procedure.…”
Section: Resultsmentioning
confidence: 99%
“…In brief, commercially available N-protected L-serine methyl ester 3 was 15 converted to the N-protected L-serine iodide methyl ester 4 in excellent yield using imidazole, PPh 3 and I 2 . 50 The solution of 4 in THF was then treated with in situ generated NaBH 2 Se 3 to afford the N-protected L-selenocystine methyl ester 5 in good yield. Due to the instability and high reactivity of selenol (SeH) 20 functional group, Secys is usually prepared as diselenide, which is reduced 51,52 in situ to the selenol when needed.…”
mentioning
confidence: 99%
“…It was found that the yield increases up to 69% in MeOH:Et 2 O = 2:3 by using two equivalents of the selenolate (i.e., MBnSe -) with respect to tosylate 6. On the other hand, when methyl ester 5 was converted into iodoalanine derivative 8 by Appel reaction 31 and subsequently into 7 under similar selenation conditions as above, but by use of only one equivalent of MBnSe -, the same product (i.e. 7) was obtained in 83% yield from 5, suggesting that the iodide is a more effective substrate than the tosylate for selenation.…”
Section: Introductionmentioning
confidence: 84%
“…When crude 8 was purified by silica gel column chromatography, the yield of 7 was decreased to 75% from 5. Identity and purity of 8 31 were confirmed by 1 …”
Section: H Nmr N-(tert-butoxycarbonyl)-se-(p-methylbenzyl)-l-selenocmentioning
confidence: 94%
“…[238] [240] und Dixneuf et al [214,215] Die Leistungsfähigkeit der chemoselektiven hydratisierenden Diin-Cyclisierung wurde durch die Totalsynthese mehrerer Cyclindricinalkaloid-Naturstoffe belegt und wird in Schema 33 am Beispiel der Synthese von Cyclindricin C (376) illustriert. [242] 6 Die Allen-Alken-Addition über Ruthenacyclopenten-Zwischenstufen…”
Section: B M Trost Et Alunclassified