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Connecting C-19 Norditerpenoids to C-20 Diterpenes : Total Syntheses of 6-Hydroxy-5,6-dehydrosugiol, 6-Hydroxysugiol, and Taiwaniaquinone H, and Formal Synthesis of Dichroanone
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
ID
462463
Author(s)
Jana, Chandan Kumar; Scopelliti, Rosario; Gademann, Karl
Connecting C-19 Norditerpenoids to C-20 Diterpenes : Total Syntheses of 6-Hydroxy-5,6-dehydrosugiol, 6-Hydroxysugiol, and Taiwaniaquinone H, and Formal Synthesis of Dichroanone
Journal
Synthesis
Volume
13
Number
13
Pages / Article-Number
2223-2232
Keywords
terpenoids, biomimetic synthesis, biosynthesis, oxidations, stereoselective synthesis, total synthesis
Abstract
Oxidation of the B-ring of abietane derivatives by Sharpless dihydroxylation gave the natural products 6-hydroxy-5,6-dehydrosugiol and 6-hydroxysugiol. Moreover, further oxidation gave a hydroxy dione derivative that provides a synthetic entry into the C-19 taiwaniaquinoid family of natural products. This route is based on biosynthetic considerations and involves a benzilic acid rearrangement followed by decarboxylation. On the basis of this approach, a total synthesis of (-)-taiwaniaquinone H and a formal synthesis of (-)-dichroanone have been achieved.
