Issue 27, 2022

Single-step construction of an acetoxypyrroloindole skeleton via tandem iodocyclization/acetoxylation of indoles

Abstract

A method for the synthesis of C3a acetoxy hexahydropyrrolo[2,3-b]indole derivatives via a PhI(OAc)2/nBu4NI mediated tandem iodocyclization/acetoxylation has been developed. The newly developed synthetic strategy features the single-step assembly of various C3a acetoxylated tetrahydropyrrole-, tetrahydrofuran-, and lactone-fused indolines under mild reaction conditions, which enabled efficient asymmetric synthesis of (−)-protubonine B.

Graphical abstract: Single-step construction of an acetoxypyrroloindole skeleton via tandem iodocyclization/acetoxylation of indoles

Supplementary files

Article information

Article type
Communication
Submitted
25 May 2022
Accepted
22 Jun 2022
First published
27 Jun 2022

Org. Biomol. Chem., 2022,20, 5397-5401

Single-step construction of an acetoxypyrroloindole skeleton via tandem iodocyclization/acetoxylation of indoles

A. Kimishima, H. Kato, K. Nakaguro and M. Arai, Org. Biomol. Chem., 2022, 20, 5397 DOI: 10.1039/D2OB01001A

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