1209497-74-4Relevant academic research and scientific papers
Synthesis of C11-desmethoxy soraphen A1α: A natural product analogue that inhibits acetyl-CoA carboxylase
Canterbury, Daniel P.,Scott, Kristen E. N.,Kubo, Ozora,Jansen, Rolf,Cleveland, John L.,Micalizio, Glenn C.
, p. 1244 - 1248 (2014/01/06)
A synthesis of C11-desmethoxy soraphen A1α is described that proceeds in just 14 steps from readily available starting materials. This natural product analogue was identified as a target of interest in a program aimed at identifying novel natural product-inspired inhibitors of acetyl-CoA carboxylase (ACC) as potential anticancer therapeutics. While describing the most efficient synthesis of a soraphen A1α analogue (total syntheses of the natural product have been reported that proceed in 25 to ≥40 linear steps), we also present data supporting the conclusion that C11-heteroatom functionality is a beneficial but unnecessary structural characteristic of soraphen A1α analogues for inhibiting ACC.
Ring-closing metathesis and photo-fries reaction for the construction of the ansamydn antibiotic kendomycin: Development of a protecting group free oxidative endgame
Magauer, Thomas,Martin, Harry J.,Mulzer, Johann
scheme or table, p. 507 - 519 (2010/05/18)
Two convergent total synthe-ses of the ansa-polyketide (-)-kendo-mycin (1) are described. The syntheses benefit from the use of readily avail-able and cheap starting materials. Highly complex diastereoselective Claisen-Ireland rearrangements were used to introduce the (E)-double bond and the C16-Me group. The ring clo-sure of the strained ansa macrocycle was achieved by ring-closing metathesis and a highly efficient combination of macrolactonization and photo-Fries re-action. A protecting group free end-game via an unstable o-quinone is pre-sented. Additionally some unsuccessful synthetic efforts towards the total synthesis of 1 are described.
