171524-04-2Relevant articles and documents
A novel strategy towards the atorvastatin lactone
Sawant, Pramod,Maier, Martin E.
experimental part, p. 9738 - 9744 (2011/02/25)
We describe a novel strategy to the atorvastatin lactone based on a Paal-Knorr synthesis of pyrrole 24 by condensing diketone 23 with primary amine 22. The latter contains the syn-1,3-diol subunit and a benzyl ether function at the other end of the chain. This allowed for manipulations on the pyrrole ring via iodination at C2, metalation with t-BuLi and carboxylation. The obtained acid 26 could be converted via amide formation, debenzylation, oxidation and lactonization to atorvastatin lactone 6. The key building block, 2-((4R,6S)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethanamine (22) was obtained by two sequential asymmetric transfer hydrogenative carbonyl allylations according to Krische.
An asymmetric synthesis of the polyol fragment of the polyene macrolide antibiotic RK-397
Fu, Fan,Loh, Teck-Peng
supporting information; experimental part, p. 3530 - 3533 (2009/10/26)
A highly convergent and asymmetric synthesis of the C11-C31 polyol fragment of RK-397 as a single isomer is accomplished via a catalytic enantioselective hetero-Diels-Alder reaction and an intermolecular olefin cross-metathesis as key steps.
Synthetic studies on the polyene macrolide antibiotics. Development of syn- and anti-1,3-diol subunits and assembly of the polyacetate region of amphotericin B
McGarvey,Mathys,Wilson,Overly,Buonora,Spoors
, p. 7778 - 7790 (2007/10/03)
The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric β-amino aldehyde (7) and the stereospecific transformat
