Total Synthesis of Gymnothelignan K via a One-Pot Homologative γ‑Butyrolactonization

The first total synthesis of tetrahydrofuran dilignan gymnothelignan K is disclosed. The approach is based on implementing an early stage one-carbon homologative lactonization, which we recently disclosed, for constructing the γ-butyrolactone scaffold with the requisite β,γ-trans-vicinal stereocente...

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Veröffentlicht in:	Organic letters 2022-04, Vol.24 (15), p.2926-2930
Hauptverfasser:	Han, Jongyeol, Choi, Hosam, Choi, Joohee, Lee, Kiyoun
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Butyrolactone Carbon Dimerization
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container_title	Organic letters
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creator	Han, Jongyeol Choi, Hosam Choi, Joohee Lee, Kiyoun
description	The first total synthesis of tetrahydrofuran dilignan gymnothelignan K is disclosed. The approach is based on implementing an early stage one-carbon homologative lactonization, which we recently disclosed, for constructing the γ-butyrolactone scaffold with the requisite β,γ-trans-vicinal stereocenters. Other salient features of the synthesis include the acid-promoted dimerization and the Suzuki–Miyaura cross-coupling reaction to install the challenging diaryl skeleton that permits the effective assembly of the optically active gymnothelignan K in 8 steps from commercially available materials.
doi_str_mv	10.1021/acs.orglett.2c00939
format	Article
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Lett</addtitle><description>The first total synthesis of tetrahydrofuran dilignan gymnothelignan K is disclosed. The approach is based on implementing an early stage one-carbon homologative lactonization, which we recently disclosed, for constructing the γ-butyrolactone scaffold with the requisite β,γ-trans-vicinal stereocenters. 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subjects	4-Butyrolactone Carbon Dimerization
title	Total Synthesis of Gymnothelignan K via a One-Pot Homologative γ‑Butyrolactonization
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