Enantioselective Total Synthesis of Chromanone Lactone Homo- and Heterodimers

Guillermo Valdomir; Soundararasu Senthilkumar; Dhandapany Ganapathy; Yun Zhang; Lutz F Tietze

doi:10.1002/asia.201800619

Enantioselective Total Synthesis of Chromanone Lactone Homo- and Heterodimers

Chem Asian J. 2018 Jul 4. doi: 10.1002/asia.201800619. Online ahead of print.

Authors

Guillermo Valdomir¹, Soundararasu Senthilkumar¹, Dhandapany Ganapathy¹, Yun Zhang¹, Lutz F Tietze¹

Affiliation

¹ Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.

PMID: 29971939
DOI: 10.1002/asia.201800619

Abstract

A one pot borylation/Suzuki-Miyaura reaction of the 4-bromochromanone lactones 21 and 23, respectively, followed by cleavage of the methyl ether moieties gave the homodimeric chromanone lactones 10 and 11. Reaction of a 1:1 mixture of 21 and 23 under otherwise identical conditions gave a 1:1:2-mixture of the two homodimers 10 and 11 and the heterodimer 12. This is the first example of the preparation of a heterodimeric chromanone lactone. For the enantioselective synthesis of the starting material, phenol 17 was transformed into the chromane 18 using a Wacker-type cyclisation with 99 % ee and 80 % yield.

Keywords: Suzuki-Miyaura reaction; Wacker oxidation; chromanones; enantioselective reactions; natural products.