Establishing a “Ring‐Size‐Divergent” Synthetic Strategy: Synthesis, Structural Revision, and Absolute Configuration of Feroniellins
نویسندگان
چکیده
Feroniellin analogs isolated from Feroniella lucida possess a furanocoumarin skeleton connected to monoterpenic five- seven-membered ethereal rings by an ether linkage and exhibit broad spectrum of biological activities. In this contribution, we intended establish “ring-size-divergent” synthetic strategy for the through chemical sythesis feroniellins. The short comprehensive synthesis feroniellins was achieved in only two steps easily available bergamottin based on strategy. addition, these syntheses resulted revision proposed structures A B determination all absolute configurations feroniellins; their preliminary anti-inflammatory activities were investigated as well.
منابع مشابه
Enantioselective total synthesis of colomitides and their absolute configuration determination and structural revision.
An efficient stereoselective synthetic approach to colomitides, 2,7-dioxabicyclo[3.2.1]octane-type natural products, is reported. Key steps are a stereocontrolled aldol reaction and a gold-catalyzed cycloisomerization. This synthetic strategy has been applied for the first asymmetric total synthesis of the proposed colomitides and their possible diastereomers. Comparison of their 1H and 13C NMR...
متن کاملCycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method.
Cycloelatanene A and B are marine natural products first reported a few years ago. Their relative structures had been elucidated by an extensive NMR study and found to be epimers. However, their absolute configurations had not been established because they were isolated in only minute quantities as oily compounds. In this study, the complete structures of cycloelatanene A and B, including absol...
متن کاملTotal synthesis and revision of the absolute configuration of seimatopolide B.
The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxylation, Yamaguchi esterification and ring-closing metathesis. This asymmetric total synthesis necessitates the revision of the originally assig...
متن کاملEstablishing the absolute configuration of the asbestinins: enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D.
A highly stereoselective synthesis of 11-acetoxy-4-deoxyasbestinin D (1) has been completed in 26 linear steps. The synthesis hinges on a selective glycolate aldol addition to establish the C-2 stereocenter, a ring-closing metathesis reaction to complete the oxonene, and an intramolecular Diels-Alder cycloaddition to establish the relative configuration at C-1, C-10, and C-14. This initial tota...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Chemistry: A European Journal
سال: 2021
ISSN: ['0947-6539', '1521-3765']
DOI: https://doi.org/10.1002/chem.202101603