861997-65-1Relevant academic research and scientific papers
Total Synthesis and Structural Assignment of (?)-Fusaequisin A
Schmidt, Ann-Christin,Hiersemann, Martin
supporting information, (2021/12/14)
(?)-Fusaequisin A is an irregularly assembled polyketide isolated from the ascomycete Fusarium equiseti. Fusaequisin A shares a carbon backbone with curvicollide C from the ascomycete Podospora curvicolla but its absolute configuration remained hitherto u
Catalytic asymmetric claisen rearrangement of gosteli-type allyl vinyl ethers: Total synthesis of (-)-9,10-dihydroecklonialactone B
Becker, Julia,Butt, Lena,Von Kiedrowski, Valeska,Mischler, Elisabeth,Quentin, Florian,Hiersemann, Martin
supporting information, p. 3040 - 3051 (2014/05/06)
The enantioselective synthesis of (-)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality a
Enantioselective synthesis of the C8-C20 segment of curvicollide C
Koerner, Marleen,Hiersemann, Martin
, p. 4979 - 4982 (2008/03/28)
The enantioselective synthesis of the C8-C20 fragment of curvicollide C has been accomplished. A catalytic asymmetric Claisen rearrangement (CAC), a diastereoselective methyl cupration of an alkynoate, and a Julia-Kocienski olefination served as key C/C-connecting transformations.
Ester dienolate [2,3]-Wittig rearrangement in natural product synthesis: Diastereoselective total synthesis of the triester of viridiofungin A, A 2, and A4
Pollex, Annett,Millet, Agnes,Mueller, Jana,Hiersemann, Martin,Abraham, Lars
, p. 5579 - 5591 (2007/10/03)
An ester dienolate [2,3]-Wittig rearrangement was utilized to access the alkylated citric acid skeleton 6 that is characteristic for the viridiofungins and other members of the alkyl citrate family of secondary natural products. The [2,3]-sigmatropic rearrangement of (Z,Z)-15 provided the rearrangement product (±)-syn-16 in moderate yield and with very good diastereoselectivity. A Julia-Kocienski olefination efficiently served to connect the polar head (±)-syn-26 with the lipophilic tail (32a-c) of the viridiofungins. Amide formation between the racemic viridiofungin precursors 35a-c and the enantiomerically pure amino acid L-tyrosine methyl ester followed by preparative reversed-phase HPLC provided the isopropyl dimethyl ester of viridiofungin A ((+)-39a), A2 ((+)-39b), and A4 ((+)-39c) as well as the nonnatural diastereomers (-)-38a-c.
