263764-23-4Relevant articles and documents
Studies toward the total synthesis of sorangicins: A shortened synthesis of the dioxabicyclo[32.1]octane core
Michaelis, Lars,Schinzer, Dieter
, p. 951 - 954 (2014)
An access to the dioxabicyclo[3.2.1]octane core of sorangicin A was developed, using a keto lactone formation, a Mukaiyama-Michael reaction and an epoxide opening as the key steps. Georg Thieme Verlag Stuttgart - New York.
SCALEABLE PREPARATION OF POLYKETIDES
-
Paragraph 0287-0290; 0358-0360, (2021/02/12)
Disclosed herein, inter alia, are methods of making polyketide compounds.
Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin
Huang, David S.,Wong, Henry L.,Georg, Gunda I.
supporting information, p. 520 - 528 (2017/04/10)
Pironetin is a natural product with potent antiproliferative activity that forms a covalent adduct with α-tubulin via conjugate addition into the natural product's α,β-unsaturated lactone. Although pironetin's α,β-unsaturated lactone is involved in its binding to tubulin, the structure–activity relationship at different positions of the lactone have not been thoroughly evaluated. For a systematic evaluation of the structure–activity relationships at the C4 and C5 positions of the α,β-unsaturated lactone of pironetin, twelve analogues of the natural product were prepared by total synthesis. Modifying the stereochemistry at the C4 and/or C5 positions of the α,β-unsaturated lactone of pironetin resulted in loss of antiproliferative activity in OVCAR5 ovarian cancer cells. While changing the C4 ethyl substituent with groups such as methyl, propyl, cyclopropyl, and isobutyl were tolerated, groups with larger steric properties such as an isopropyl and benzyl groups were not.
