645386-89-6Relevant articles and documents
Directed orthometalation and the asymmetric total synthesis of N -deoxymilitarinone A and torrubiellone B
Ding, Feiqing,William, Ronny,Leow, Min Li,Chai, Hua,Fong, Jacqueline Zi Mei,Liu, Xue-Wei
, p. 26 - 29 (2014/01/23)
A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.
Stereoselective synthesis of a monocyclic peloruside A analogue
Wulischleger, Christoph W.,Gertsch, Juerg,Altmann, Karl-Heinz
supporting information; experimental part, p. 1120 - 1123 (2010/06/13)
Chemical Equation Presentation The stereoselective synthesis of the monocyclic peloruside A analogue 4 has been achieved, following a new efficient approach for the introduction of the side chain, involving a late-stage addition of vinyl lithium species 7a to aldehyde 8. Further key steps are a highly diastereoselective allyltitanation reaction and a RCM-based macrocyclization.
Quasiracemic synthesis: Concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine
Zhang, Qisheng,Rivkin, Alexey,Curran, Dennis P.
, p. 5774 - 5781 (2007/10/03)
The concept of quasiracemic synthesis is introduced and illustrated with syntheses of both enantiomers of pyridovericin (whose absolute configuration is assigned as R) and mappicine. Like racemic synthesis, quasiracemic synthesis provides both enantiomers in a single synthetic sequence; however, separation tagging is used to ensure that quasiracemic mixtures can be analyzed, separated, and identified on demand. Fluorous tags of differing chain lengths are used to tag two enantiomeric starting materials. The resulting quasienantiomers are mixed to make a quasiracemate, which is then treated like a true racemate in successive steps of the synthesis. Fluorous chromatography is used to separate, or demix, the final quasiracemate into its two components, which are then detagged to provide (true) enantiomeric products. Quasiracemic synthesis is portrayed as the first and simplest of a series of mixture synthesis techniques based on separation tagging, and the prospects for using other types of separation tags are briefly evaluated.
