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- Title
One‐Step Synthesis of Norabietane Core and its Alkylation to Abietane Analogs.
- Authors
Seong, Chaehyeon; Kang, Juyeon; Lee, Junseong; Oh, Chang Ho
- Abstract
Keywords: Norabietane; Abietane; Copper catalysis; Organometallic reactions; Stereoselective cyclization; Organic synthesis EN Norabietane Abietane Copper catalysis Organometallic reactions Stereoselective cyclization Organic synthesis 517 520 4 03/22/21 20210301 NES 210301 Synthesis of norabietane core. GLO:1CJF/01mar21:bkcs12222-fig-0006.jpg PHOTO (COLOR): 3 Mechanism of copper-catalyzed cyclization to cis-fused tricycle 4. gl Third, we selected LDA as a base to effectively introduce several functional groups at the C-10 position of B 4 b . Tu I et al i . reported the intermediate of pisiferic acid starting from 2,7-dihydroxynaphthalene which was converted to -ketoester B c b , by three-steps: Birch-reduction, hydrolysis, and carboxylation. Pan I et al i . obtained carnosic acid analog from bicyclic intermediate B e b obtained from alkylation of 5,5-dimethyl-1,3-cyclohexanedione with 2-substituted aryl iodethane.11a Most of the cyclization methods are performed by intramolecular Friedel-Crafts cyclization using Lewis acid in Majetich's pioneering work.11b In the final case, several abietanes have been synthesized from pre-existing abietane cores ( B f b or B g b ) by functional group modification.
- Subjects
ALKYLATION; ABIETANE; CYCLIC compounds; BENZYL group; INTRAMOLECULAR catalysis; GOLD catalysts; ETHYL acetate
- Publication
Bulletin of the Korean Chemical Society, 2021, Vol 42, Issue 3, p517
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.12222