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Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation

Gisela V. Saborit, Carlos Cativiela, Ana I. Jiménez, Josep Bonjoch and Ben Bradshaw

Beilstein J. Org. Chem. 2018, 14, 2597–2601. https://doi.org/10.3762/bjoc.14.237

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Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation

Gisela V. Saborit, Carlos Cativiela, Ana I. Jiménez, Josep Bonjoch and Ben Bradshaw

Beilstein J. Org. Chem. 2018, 14, 2597–2601. https://doi.org/10.3762/bjoc.14.237

How to Cite

Saborit, G. V.; Cativiela, C.; Jiménez, A. I.; Bonjoch, J.; Bradshaw, B. Beilstein J. Org. Chem. 2018, 14, 2597–2601. doi:10.3762/bjoc.14.237

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TY  - JOUR
A1  - Saborit, Gisela V.
A1  - Cativiela, Carlos
A1  - Jiménez, Ana I.
A1  - Bonjoch, Josep
A1  - Bradshaw, Ben
T1  - Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation
JF  - Beilstein Journal of Organic Chemistry
PY  - 2018///
VL  - 14
SP  - 2597
EP  - 2601
SN  - 1860-5397
DO  - 10.3762/bjoc.14.237
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.14.237
KW  - alkaloid
KW  - Danheiser annulation
KW  - decahydroquinoline
N2  - A straightforward synthetic entry to functionalized hydrindane compounds based on a rapid assembly of the core nucleus by a Danheiser cycloaddition is reported. Valuable bicyclic building blocks containing the fused five and six-membered carbocyclic ring system can be achieved in only four steps from a simple acyclic β-keto ester.
ER  -

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Survase, V. U.; Handore, K. L. Stereoselective Strategies for the Synthesis of Functionalized Cis‐Hydrindanes in Natural Product Synthesis. European Journal of Organic Chemistry 2025, 28. doi:10.1002/ejoc.202500006
Roberts, D. D.; McLaughlin, M. G. Strategic Applications of the β‐Silicon Effect. Advanced Synthesis & Catalysis 2022, 364, 2307–2332. doi:10.1002/adsc.202200237
De, S. K. doi:10.1002/9783527828166.ch4
Jeon, H.; Winkler, J. D. Synthesis of Cyclohexane-Angularly-Fused Triquinanes. Synthesis 2020, 53, 475–488. doi:10.1055/s-0040-1705953
Xu, B.; Xun, W.; Su, S.; Zhai, H. Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol. Angewandte Chemie 2020, 132, 16617–16621. doi:10.1002/ange.202007247
Xu, B.; Xun, W.; Su, S.; Zhai, H. Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol. Angewandte Chemie (International ed. in English) 2020, 59, 16475–16479. doi:10.1002/anie.202007247
Beļaunieks, R.; Puriņš, M.; Turks, M. Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift. Synthesis 2020, 52, 2147–2161. doi:10.1055/s-0039-1690898

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