Asymmetric Total Synthesis of Lepadiformine C Using Memory of Chirality in an Intramolecular Ester Enolate Michael Addition

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• 作者：Seokwoo Lee ; Minsik Bae ; Jinkyung In ; Jae Hyun Kim ; Sanghee Kim
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：19
• 期：1
• 页码：254-257
• 全文大小：397K
• ISSN：1523-7052

文摘

The asymmetric synthesis of lepadiformine C was achieved using d-proline as the only chiral source. The synthetic strategy features the use of the principle of “memory of chirality” in an intramolecular Michael addition to construct the bicyclic intermediate without the aid of external chiral sources. A brief mechanistic rationale is presented to account for the stereochemical outcome.