TY - CHAP
T1 - Complex Natural Products Derived from Pyrogallols
AU - Novak, Alexander J.E.
AU - Trauner, Dirk
N1 - Publisher Copyright:
© 2022, The Author(s), under exclusive license to Springer Nature Switzerland AG.
PY - 2022
Y1 - 2022
N2 - Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.
AB - Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.
KW - Cascades
KW - Cycloadditions
KW - Fungal metabolites
KW - Pyrogallols
KW - Racemic natural products
KW - o-Quinones
UR - http://www.scopus.com/inward/record.url?scp=85128135793&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85128135793&partnerID=8YFLogxK
U2 - 10.1007/978-3-030-92030-2_1
DO - 10.1007/978-3-030-92030-2_1
M3 - Chapter
C2 - 35416516
AN - SCOPUS:85128135793
T3 - Progress in the Chemistry of Organic Natural Products
SP - 1
EP - 46
BT - Progress in the Chemistry of Organic Natural Products
PB - Springer Science and Business Media Deutschland GmbH
ER -