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1.
Smooth isoindolinone formation from isopropyl carbamates via Bischler-Napieralski-type cyclization.
Adachi, Satoshi; Onozuka, Masao; Yoshida, Yuko; Ide, Mitsuaki; Saikawa, Yoko; Nakata, Masaya.
Org Lett ; 16(2): 358-61, 2014 Jan 17.
Article in English | MEDLINE | ID: mdl-24364475

ABSTRACT

Isopropyl carbamates derived from benzylamines provide isoindolinones by treatment with phosphorus pentoxide at room temperature. Utility of this Bischler-Napieralski-type cyclization and a new mechanism involving a carbamoyl cation for rationalization of this smooth conversion are discussed.


Subject(s)
Benzylamines/chemistry , Carbamates/chemistry , Indoles/chemical synthesis , 2-Propanol/chemistry , Cyclization , Esters , Indoles/chemistry , Molecular Structure , Phosphorus Compounds/chemistry , Temperature
2.
Total syntheses of lactonamycin and lactonamycin Z with late-stage A-ring formation and glycosylation.
Adachi, Satoshi; Watanabe, Kana; Iwata, Yusuke; Kameda, Shunsuke; Miyaoka, Yoshihito; Onozuka, Masao; Mitsui, Ryo; Saikawa, Yoko; Nakata, Masaya.
Angew Chem Int Ed Engl ; 52(7): 2087-91, 2013 Feb 11.
Article in English | MEDLINE | ID: mdl-23303690

Subject(s)
Indoles/chemical synthesis , Naphthoquinones/chemical synthesis , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Carbamates/chemistry , Catalysis , Coordination Complexes/chemistry , Cyclization , Glycosylation , Indoles/chemistry , Naphthoquinones/chemistry , Polyketides/chemical synthesis , Polyketides/chemistry
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