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Mechanistic study of the spiroindolones: a new class of antimalarials.

ABSTRACT: During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds.

SUBMITTER: Zou B

PROVIDER: S-EPMC6268731 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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Mechanistic study of the spiroindolones: a new class of antimalarials.

Zou Bin B Yap Peiling P Sonntag Louis-Sebastian LS Leong Seh Yong SY Yeung Bryan K S BK Keller Thomas H TH

Molecules (Basel, Switzerland) 20120824 9

During the synthesis of the new antimalarial drug candidate NITD609, a high degree of diastereoselectivity was observed in the Pictet-Spengler reaction. By isolating both the 4E and 4Z imine intermediates, a systematic mechanistic study of the reaction under both kinetic and thermodynamic conditions was conducted. This study provides insight into the source of the diastereoselectivity for this important class of compounds. ...[more]

PMID: 22922283

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