Synthesis of the indeno[1,2-b]indole core of janthitrem B

文献情報

出版日 2023-11-02

DOI 10.1039/D3OB01566A

インパクトファクター 3.876

著者

Marvin Fresia, Alexandra Dierks, Peter G. Jones, Thomas Lindel

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要旨

The tetracyclic core structure of the majority of indole diterpenoids features a trans-hydrindane moiety that is fused to an indole unit. We report here a novel synthetic route that includes a photo-Nazarov cyclization of a 3-acylindole precursor initially providing the thermodynamically preferred cis-hydrindanone. After reduction and conversion to the cyclopentadiene, dihydroxylation and hydrogenation provided the indoline. The key step generated the trans-system by stereospecific hydride shift on a dioxaphospholane under Grainger's conditions, for the first time applied to an N-heterocycle. When starting from the corresponding indole, we observed the formation of hitherto unknown methanocyclohepta[b]indolones. Deoxygenation of the trans-hydrindanone was achieved after conversion to the 1,3-dithiolane, followed by RANEY® Ni reduction.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.