Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Sep 1;51(35):4653-4654.
doi: 10.1016/j.tetlet.2010.06.135.

Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates

Jun Hee Lee  1 , Samuel J Danishefsky
Affiliations

Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates

Jun Hee Lee et al. Tetrahedron Lett. .

Abstract

We have developed an efficient Lewis acid-catalyzed Diels-Alder route to a series of cis-fused bicyclic ketones bearing quaternary halogenation at the angular position. We have also developed a Diels-Alder based one-flask method for the regioselective preparation of TBS-protected 6-hydroxy tetralone and 5-hydroxy indanone derivatives.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. For the preparation of 2-halocycloalk-2-enones, see: Krafft ME, Cran JW. Synlett. 2005:1263–1266.. Kim K-M, Park I-H. Synthesis. 2004:2641–2644.. Anderson JC, Pearson DJ. J. Chem. Soc., Perkin Trans. 1998;1:2023–2029.. Kim KM, Chung KH, Kim EK, Ryu EK. Synthesis. 1993:283–284.. Smith AB, III, Branca SJ, Pilla NN, Guaciaro MA. J. Org. Chem. 1982;47:1855–1869..

    1. Liu H-J, Shia K-S. Tetrahedron Lett. 1995;36:1817–1820.

    2. For an earlier report on the Diels–Alder reaction of 1d with Dane's diene under SnCl4 catalysis: Woski SA, Koreeda M. J. Org. Chem. 1992;57:5736–5741..

    1. An elegant enantioselective version of the related reaction was reported during investigation of this work: Shibatomi K, Futatsugi K, Kobayashi F, Iwasa S, Yamamoto H. J. Am. Chem. Soc. 2010;132:5625–5627..

    1. Lee JH, Kim WH, Danishefsky SJ. Tetrahedron Lett. 2009;50:5482–5484. - PMC - PubMed

    1. All new compounds gave satisfactory analytical data (mp, IR, 1H NMR, 13C NMR, and high resolution mass). See Supplementary Data for experimental and analytical details.

LinkOut - more resources