519176-52-4Relevant academic research and scientific papers
Precursor directed biosynthesis of novel 6-deoxyerythronolide B analogs containing non-natural oxygen substituents and reactive functionalities
Hunziker, Daniel,Wu, Nicholas,Kenoshita, Kenji,Cane, David E.,Khosla, Chaitan
, p. 635 - 638 (1999)
Feeding of synthetic precursors to a blocked mutant of 6- deoxyerythronolide B synthase (DEBS) [1] led to production of novel 6- deoxyerythronolide B analogs in vivo containing additional non-natural oxygen substituents as well as additional reactive groups.
Substrate-controlled stereoselectivity in the Yamamoto aldol reaction
Schl?ger, Nadin,Kirschning, Andreas
supporting information, p. 7721 - 7729 (2013/04/23)
The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products. The Royal Society of Chemistry 2012.
Synthesis of the macrolactone of migrastatin and analogues with potent cell-migration inhibitory activity
Dias, Luiz C.,Finelli, Fernanda G.,Conegero, Leila S.,Krogh, Renata,Andricopulo, Adriano D.
, p. 6748 - 6759 (2011/03/21)
The synthesis of the macrolactone core of migrastatin 2, its potent anti-metastasis analogue 34, and ester derivatives 35 and 38 are reported. The approach involves the use of a dihydroxylation reaction to establish the desired C-8 stereocenter followed by a metathesis cyclization reaction. The effects of the compounds on the migration and invasion of human breast cancer cells were evaluated by using the wound-healing and the Boyden-chamber cell-migration and cell-invasion assays. The results revealed a high potency of the macrolactones 2 and 34 and the ester analogues 35 and 38, which suggests they have potential as antimetastatic agents. The synthesis of macrolactones 2 and 34 as well as esters 35 and 38 proceeds in good overall yields. Macrolactone 34 and ester 38 are amongst the most active compoundsof the migrastatin family prepared so far and show good promise as anticancer compounds. Copyright
A short approach to trisubstituted γ-butyrolactones
Dias, Luiz C.,De Castro, Ilton B. D.,Steil, Leonardo J.,Augusto, Tatiana
, p. 213 - 216 (2007/10/03)
The dihydroxylation of unsaturated aldol adducts with catalytic OsO 4 and NMO occurs under very mild conditions and with moderate to excellent levels of diastereoselectivity to give trisubstituted γ-butyrolactone derivatives.
