122547-72-2Relevant articles and documents
Total Synthesis of the Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis
Krische, Michael J.,Schempp, Tabitha T.
, p. 1016 - 1022 (2022/02/05)
The total synthesis of soraphen A, a myxobacterial metabolite and inhibitor of acetyl CoA carboxylase, was completed in 11 steps (longest linear sequence), less than half the steps previously required. Seven metal-catalyzed processes were deployed to unlock step-economy (comprising five asymmetric processes and four C-C bond formations). The present route does not utilize chiral auxiliaries, and four of five C-C bond formations exploit non-premetalated partners. To maximize convergency, an asymmetric Tsuji reduction was developed using a Pd-AntPhos catalyst that allows a metathesis-inactive allylic carbonate to serve as a masked terminal olefin, thereby enabling successive olefin metathesis events.
Total synthesis of soraphen A(1α)
Abel, Stephan,Faber, Dominik,Hueter, Ottmar,Giese, Bernd
, p. 188 - 197 (2007/10/03)
The convergent synthesis of macrolide soraphen A(1α) is described starting from glucose (western part) and mannose (eastern part). Mannose was converted into a 2-deoxyribohexopyranoside that could be methylated and reduced stereoselectively. Chain elongation at C-6 was carried out by stereoselective addition of a magnesium acctylide. The two fragments (western and eastern) were assembled by a Julia olefination followed by macrolactonization. The introduction of the methyl group at C-2 of norsoraphen occurred stereoselectively for thermodynamic reasons.
Totalsynthese von Soraphen A1α
Abel, Stephan,Faber, Dominik,Hueter, Ottmar,Giese, Bernd
, p. 2522 - 2523 (2007/10/02)
-
