title: Directed orthometalation and the asymmetric total synthesis of N-deoxymilitarinone A and torrubiellone B.
abstract: 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.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637371.
authors.forename: Feiqing
authors.initials: F
authors.lastname: Ding
authors.forename: Ronny
authors.initials: R
authors.lastname: William
authors.forename: Min Li
authors.initials: ML
authors.lastname: Leow
authors.forename: Hua
authors.initials: H
authors.lastname: Chai
authors.forename: Jacqueline Zi Mei
authors.initials: JZ
authors.lastname: Fong
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; C587989:N-deoxymilitarinone A; D011728:Pyridones; C587988:torrubiellone B