1198778-15-2Relevant academic research and scientific papers
Total synthesis of mycestericin A and its 14-epimer
Yamanaka, Hiroyoshi,Sato, Kazuya,Sato, Hideyuki,Iida, Masatoshi,Oishi, Takeshi,Chida, Noritaka
, p. 9188 - 9201 (2009)
The total synthesis of mycestericin A (1) and its 14-epimer 34 is described herein. The Overman rearrangement of an allylic trichloroacetimidate derived from l-tartrate generated a tetra-substituted carbon with nitrogen and subsequent stereoselective transformations afforded the highly functionalized left-half segment, vinyl iodide. Cross-coupling of the vinyl iodide with a chiral organometallic species synthesized from d-tartrate under the Negishi or Suzuki-Miyaura coupling conditions, followed by deprotection, completed the total synthesis of 1. The 14-epimer of mycestericin A was also synthesized, and a comparison of [α]D values of peracetyl γ-lactone derivatives of mycestericin A and its 14-epimer as well as degradation studies of 1 and 34 fully confirmed the proposed absolute structure of mycestericin A.
