667419-33-2Relevant academic research and scientific papers
Asymmetric synthetic study of macrolactin analogues
Kobayashi, Yusuke,Fukuda, Akihiro,Kimachi, Tetsutaro,Ju-ichi, Motoharu,Takemoto, Yoshiji
, p. 2607 - 2622 (2007/10/03)
We designed two aromatic analogues 1a and 1b of macrolactin A with expectation of enhancing biological activity and metabolical stability. As a result of retrosynthetic analysis of these compounds 1a-b, two synthetic strategies have been examined. The first strategy includes the enantioselective addition of nonadienyl anion, derived from 3, to aldehyde 4 as a key step. The second one includes epimerization of ynone 7 to (E,E)-conjugated dienone 31 and subsequent diastereoselective hydride-reduction of 31. Although the former route furnished no desired target, the latter one was revealed to work well for the synthesis of 1. Unfortunately, the aimed (2Z,4E)-analogue 1a could not be synthesized due to an epimerization of the (2Z)-olefin into the (2E)-olefin. However, these methods could be applied to the total asymmetric synthesis of the (2E,4E)-analogue 1b. Overall, control of all of the four stereocenters was achieved by means of asymmetric and diastereoselective reactions without using any chiral natural sources.
Asymmetric synthesis of macrolactin analogue
Kobayashi, Yusuke,Fukuda, Akihiro,Kimachi, Tetsutaro,Ju-ichi, Motoharu,Takemoto, Yoshiji
, p. 677 - 680 (2007/10/03)
Total asymmetric synthesis of macrolactin A analogue was accomplished by the convergent strategy. Rapid access to advanced intermediate 16 through isomerization of ynone to (E,E)-conjugated dienone is a key step of this synthesis. Overall, control of all
