405297-50-9Relevant academic research and scientific papers
Stereocontrolled synthesis of (-)-macrolactin A
Marino, Joseph P.,McClure, Michael S.,Holub, David P.,Comasseto, Joao V.,Tucci, Fabio C.
, p. 1664 - 1668 (2007/10/03)
The total synthesis of (-)-macrolactin A, a 24-membered macrolide, has been achieved using a newly developed 1,3-diol synthon for the introduction of two key stereogenic centers. The synthon was derived from sequential use of the Noyori asymmetric reduction followed by chiral sulfoxide methodology. Tellurium-derived cuprate organometallics offered an efficient and highly stereoselective means for installation of the C8 Z/E-diene, while the C15 E/E-segment was derived from a Julia-Lythgoe olefination. Yamaguchi lactonization was used to secure the macrocycle in a convergent approach with the longest linear sequence of 19 steps from Noyori alcohol 6.
