149117-84-0Relevant academic research and scientific papers
Formal total synthesis of camptothecin via ring-closing metathesis strategy
Chavan, Subhash P.,Pasupathy,Venkatraman,Kale, Ramesh R.
, p. 6879 - 6882 (2004)
A formal total synthesis of camptothecin 1 is presented. The key steps include construction of the D-ring of camptothecin featuring an efficient ring-closing metathesis (RCM) reaction and the subsequent Michael addition of nitropropane across the double b
Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis
Bendelsmith, Andrew J.,Kim, Seohyun Chris,Wasa, Masayuki,Roche, Stéphane P.,Jacobsen, Eric N.
, p. 11414 - 11419 (2019/08/20)
We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.
Arginase Inhibitors and Their Therapeutic Applications
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Paragraph 1091; 1094; 1095, (2017/11/29)
Disclosed are small molecule therapeutic compounds that are potent inhibitors of arginase 1 and arginase 2 activity. Also disclosed are pharmaceutical compositions comprising the compounds, and methods for using the compounds for treating or preventing a
Total synthesis of (+)-camptothecin via an intramolecular palladium-catalyzed cyclization strategy
Chavan, Subhash P.,Pathak, Ashok B.,Kalkote, Uttam R.
, p. 2635 - 2638 (2008/02/12)
The novel cascade intramolecular Pd-catalyzed cyclization followed by aromatization for the construction of D ring of (+)-camptothecin as a key step is demonstrated. Georg Thieme Verlag Stuttgart.
A practical and efficient synthesis of (±)- camptothecin
Chavan, Subhash P.,Venkatraman
, p. 6745 - 6748 (2007/10/03)
A practical and efficient synthesis of (±)-camptothecin from glycine via an intramolecular Michael addition is described.
