907593-86-6Relevant 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
supporting information, 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.
A stereoselective synthesis of the C11-C19 fragment of (+)-peloruside A
Chen, Zhen-liang,Zhou, Wei-shan
, p. 5289 - 5292 (2007/10/03)
A new route to the synthesis of the C11-C19 fragment of peloruside A is described, which includes an aldol reaction with ethyl acetoacetate, β-hydroxyl-directed reduction of β-hydroxy ketone, as well as methylation of C13 hydroxyl moiety in the system of
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.
