1209497-40-4Relevant academic research and scientific papers
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.
