Intramolecular TDDA Approach to the Dihydrobenzopentalene Skeleton of Aromatized Nine-Membered Enediyne Antibiotics.

Authors

Chiharu Suzuki, Kota Asano, Hideaki Takano, Norihito Fukui, Hiroshi Shinokubo, Toshio Nishikawa

Published in

The Journal of organic chemistry. Aug 31, 2026. Epub Aug 31, 2026.

Abstract

The tetradehydro-Diels-Alder (TDDA) reaction has recently emerged as a powerful method for the construction of polycyclic frameworks. In this study, we investigated the application of the TDDA reaction to the synthesis of the nine-membered enediyne framework found in enediyne antibiotics and its aromatized product, the tetradehydrobenzopentalene skeleton. Several TDDA precursors bearing an acetylene carboxylic acid moiety and an enyne side chain on a cyclopentene core were synthesized via two Pd-catalyzed reactions. Heating these precursors at 150 °C did not afford the expected TDDA product. However, a hetero-TDDA reaction occurred at 150 °C to give a tricyclic compound containing a pyrone moiety when the silyl ester was employed. In contrast, the precursor with interchanged side chains produced a TDDA adduct with a dihydrobenzopentalene framework, albeit in low yield upon heating at 200 °C.

PMID:
42686634
Bibliographic data and abstract were imported from PubMed on 03 Sep 2026.

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