Issue 18, 2023

Convenient synthesis of perhydrobenz[e]indene triketone, a key intermediate for the total synthesis of stelletins

Abstract

A complementary strategy for the formal total synthesis of (±)-stelletins is reported. Key reactions include a diastereoselective Eschenmoser–Claisen rearrangement, a highly diastereoselective alkylation of decalin-nitrile, and an intramolecular [3 + 2] cycloaddition/N–O reductive bond cleavage to construct the strained functionalized tricyclic core of (±)-stelletins.

Graphical abstract: Convenient synthesis of perhydrobenz[e]indene triketone, a key intermediate for the total synthesis of stelletins

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2023
Accepted
14 Apr 2023
First published
20 Apr 2023

Org. Biomol. Chem., 2023,21, 3850-3857

Convenient synthesis of perhydrobenz[e]indene triketone, a key intermediate for the total synthesis of stelletins

Y. Cao, X. Liu, Z. Wang, Y. Wang, X. Jiao and P. Xie, Org. Biomol. Chem., 2023, 21, 3850 DOI: 10.1039/D3OB00319A

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