ArticleThe Journal of organic chemistry2009
Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.
Article in The Journal of organic chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 51 citations in OpenAlex.
- Synthetic studies of viridiofungins, broad-spectrum antifungal agents and serine palmitoyl transferase inhibitors.The Journal of antibiotics · 2017Review
- An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921.Tetrahedron letters · 2016Article
- Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.Journal of the American Chemical Society · 2014Article
- FeClTetrahedron letters · 2014Article
- A stereoselective synthesis of (-)-viridiofungin A utilizing a TiCl(4)-promoted asymmetric multicomponent reaction.Organic letters · 2012Article
- Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.The Journal of organic chemistry · 2010Article
- A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.Organic letters · 2010Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
An asymmetric synthesis of anti-aldol segments via a nonaldol route is described. The strategy involves a highly diastereoselective synthesis of functionalized tetrahydrofuran derivatives from optically active 4-phenylbutyrolactone. Treatment of the tetrahydrofuran derivatives with a Lewis acid and acetic anhydride provided the corresponding ring-opened styrene derivatives. Oxidative cleavage of the styrene derivatives provided access to the anti-aldol segments. The utility of this methodology was demonstrated by the synthesis of statine derivatives and pancreatic lipase inhibitor, (-)-tetrahydrolipstatin.
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Registered trials
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