1426140-07-9Relevant academic research and scientific papers
Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones
Fernandes, Rodney A.,Kumar, Praveen,Saini, Deepak
, p. 18976 - 18982 (2021/10/29)
A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed through the chiral pool material,l-aspartic acid. Next, the allylation reaction was strategically utilized to provide the requisite olefin bond for the intended ring-closing metathesis, allowing the installation of the remaining dihydro-α-pyrone moiety in the natural products. It also enabled the targeting of both dihydro-α-pyrone diastereomers. Thus, the first stereoselective total synthesis of (+)-7′,8′-dihydroobolactone was accomplished, establishing its structure and absolute configuration.
Enantioselective synthesis of (+)-obolactone based on a symmetry-breaking wacker monooxidation of a diene
Walleser, Patrick,Brückner, Reinhard
supporting information, p. 1294 - 1297 (2013/05/21)
A concise synthesis of the dihydro-α-pyrone/dihydro-γ-pyrone natural product (+)-obolactone (13) is disclosed. The dienediol acetonide 23 (≥97% ee) was obtained from 1,5-dichloropentane-2,4-dione in four steps. A Wacker monooxidation of 23 furnished the monoketone 24 in 64% yield. The OH group of the ensuing dihydro-γ-pyrone 31 was esterified under Mitsunobu conditions with cinnamic acid (→ 80% inversion and 20% retention of configuration). A ring-closing metathesis formed the dihydro-α-pyrone moiety of the target in the terminating step.
