391208-05-2Relevant academic research and scientific papers
Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy
Wrobleski, Aaron,Sahasrabudhe, Kiran,Aube, Jeffrey
, p. 5475 - 5481 (2004)
Total syntheses of alkaloid 251F (1), a natural product detected from the skin extracts of the dendrobatid frog species Minyobates bombetes, and its racemic 3-desmethyl derivative (2) are reported. A Diels-Alder reaction initiated both syntheses and established four consecutive stereogenic centers. Important to the synthesis of 2 was a first-generation ozonolysis/olefination/aldol strategy to convert a [2.2.1] bicyclic acid to the [3.3.0]bicyclooctane diquinane 4b. Further elaboration to an appropriate keto azide allowed for a key intramolecular Schmidt reaction to deliver the tricyclic core of the target molecule. In a second-generation approach, a tandem ring-opening/ring-closing metathesis reaction effected an overall [2.2.1] → [3.3.0] skeletal rearrangement to deliver diquinane 4a. In similar fashion, 4a was manipulated to an appropriate keto azide, and an intramolecular Schmidt reaction generated the core cyclic architecture of 251F.
Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid
Chatterjee, Bhaskar,Mondal, Dhananjoy,Bera, Smritilekha
, p. 1170 - 1185,16 (2020/09/09)
A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores.
Probing the influence of an allylic methyl group in zearalenone analogues on binding to Hsp90
Rink, Christian,Sasse, Florenz,Zubrienae -, Asta,Matulis, Daumantas,Maier, Martin E.
, p. 14469 - 14478 (2011/03/21)
By the replacement of an acetate with propionate by means of organic synthesis, a range of zearalenone analogues were prepared that feature an allylic methyl group. For the synthesis of the aliphatic region of the analogues, we used an asymmetric alkylati
Highly stereoselective approach toward the synthesis of the macrolactone core of amphidinolide W
Mohapatra, Debendra K.,Chatterjee, Bhaskar,Gurjar, Mukund K.
body text, p. 755 - 758 (2009/05/07)
The diastereoselective synthesis of the macrolactone core of amphidinolide W was successfully accomplished using Evans' asymmetric alkylation, Aldol reaction, Julia-Kocienski olefination, and Kita's macrocyclization protocol.
