Frick Laboratory, Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
Org Lett. 2011 Oct 7;13(19):5164-7. doi: 10.1021/ol2020362. Epub 2011 Sep 6.
A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6-disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.
本文披露了一种从手性、易得的起始原料简洁、立体控制合成 citrinadin B 核心结构的方法。其亮点包括可方便获得环状色氨酸互变异构体和反式-2,6-二取代哌啶片段、高效、立体保持的混合 Claisen 酰化反应用于这些片段的偶联，以及进一步的非对映选择性羰基加成和氧化重排用于核心结构的组装。
