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Cationic cyclizatio...
Cationic cyclization of 2-alkenyl-1,3-dithiolanes: DiastereoselectiveSynthesis of trans-decalins
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- Goncalves, Sylvie (författare)
- Universite de Strasbourg, Faculte de Pharmacie UMR/CNRS 7199, Laboratoire des Systemes Chimiques Fonctionnels, Illkirch, France
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- Santoro, Stefano (författare)
- Stockholms universitet,Institutionen för organisk kemi
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- Nicolas, Marc (författare)
- Les Laboratoires Pierre Fabre, Centre de Developpement Chimique et Industriel, Gaillac, France
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- Wagner, Alain (författare)
- Universite de Strasbourg, Faculte de Pharmacie UMR/CNRS 7199, Laboratoire des Systemes Chimiques Fonctionnels, Illkirch, France
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- Maillos, Philippe (författare)
- Les Laboratoires Pierre Fabre, Centre de Developpement Chimique et Industriel, Gaillac, France
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- Himo, Fahmi (författare)
- Stockholms universitet,Institutionen för organisk kemi
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- Baati, Rachid (författare)
- Universite de Strasbourg, Faculte de Pharmacie UMR/CNRS 7199, Laboratoire des Systemes Chimiques Fonctionnels, Illkirch, France
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(creator_code:org_t)
- 2011-04-13
- 2011
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society. - 0022-3263 .- 1520-6904. ; 76:9, s. 3274-3285
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- An unprecedented and highly diastereoselective 6-endo-trig cyclization of 2-alkenyl-1,3-dithiolanes has beendeveloped yielding trans-decalins, an important scaffold present in numerous di- and triterpenes. The novelty of this 6-endo-trigc yclization stands in the stepwise mechanism involving 2-alkenyl-1,3-dithiolane, acting as a novel latent initiator. It is suggested that the thioketal opens temporarily under the influence of TMSOTf, triggering the cationic 6-endo-trig cyclization, andcloses after C−C bond formation and diastereoselective protonation to terminate the process. DFT calculations confirm this mechanistic proposal and provide a rationale for the observed diastereoselectivity. The reaction tolerates a wide range of functionalities and nucleophilic partners within the substrate. We have also shown that the one-pot 6-endo-trig cyclization followedby in situ 1,3-dithiolane deprotection afford directly the corresponding ketone. This improvement allowed the achievement of the shortest total synthesis of triptophenolide and the shortest formal synthesis of triptolide.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Organic chemistry
- Organisk kemi
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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