title: Iterative direct aldol strategy for polypropionates: enantioselective total synthesis of (-)-membrenone A and B.
abstract: An iterative direct aldol reaction using a C3 propionate unit as an aldol donor offers expeditious access to polyketide assembly in a highly diastereo- and enantioselective manner. An all-syn polyketide array with four consecutive stereogenic centers was efficiently constructed by an aldol reaction of thiopropionamide via soft Lewis acid/hard Brønsted base cooperative catalysis. This iterative aldol strategy led to an enantioselective synthesis of (-)-membrenone A and B.
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN), Tokyo , 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Kaliyamoorthy
authors.initials: K
authors.lastname: Alagiri
authors.forename: Shaoquan
authors.initials: S
authors.lastname: Lin
authors.forename: Naoya
authors.initials: N
authors.lastname: Kumagai
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D008386:Marine Biology; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D011422:Propionates; D011753:Pyrones; C430548:membrenone A; C430549:membrenone B; C116609:3-hydroxybutanal