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
. 2022 Jul 5;13(30):8871-8875.
doi: 10.1039/d2sc02541h. eCollection 2022 Aug 4.

Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones

Yi Li  1 , Shuang Xin  1 , Rui Weng  1 , Xiaohua Liu  1 , Xiaoming Feng  1
Affiliations

Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones

Yi Li et al. Chem Sci. .

Abstract

Chiral chromanone lactones are a class of natural products with important biological activity. We report a direct diastereo- and enantioselective vinylogous conjugate addition of butenolide to 2-ester substituted chromones. The transformation proceeded well in the presence of as low as 1 mol% of a chiral N,N'-dioxide/ScIII complex, 3 Å MS and a catalytic amount of hexafluoroisopropanol (HFIP). The scope of Michael acceptors includes a variety of substituted chromones at different positions, and the desired chromanone lactones upon reduction are afforded in good yield and diastereoselectivity, and excellent enantioselectivity (up to 99% ee). The strategy could be used in the concise synthesis of blennolide C and gonytolide A, C and G.

PubMed Disclaimer

Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Background information about chromanone lactones and related compounds.
Scheme 2
Scheme 2. The gram scale synthesis of 3a and transformations into natural products.
Scheme 3
Scheme 3. Proposed explanation for the role of additives and selectivity.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. McPhee F. Caldera P. S. Bemis G. W. McDonagh A. F. Kuntz I. D. Craik C. S. Biochem. J. 1996;320:681. doi: 10.1042/bj3200681. - DOI - PMC - PubMed
    2. Bräse S. Encinas A. Keck J. Nising C. F. Chem. Rev. 2009;109:3903. doi: 10.1021/cr050001f. - DOI - PubMed
    3. Siddiqui I. N. Zahoor A. Hussain H. Ahmed I. Ahmad V. U. Padula D. Draeger S. Schulz B. Meier K. Steinert M. Kurtán T. Flörke U. Pescitelli G. Krohn K. J. Nat. Prod. 2011;74:365. doi: 10.1021/np100730b. - DOI - PubMed
    4. Kikuchi H. Isobe M. Sekiya M. Abe Y. Hoshikawa T. Ueda K. Kurata S. Katou Y. Oshima Y. Org. Lett. 2011;13:4624. doi: 10.1021/ol2018449. - DOI - PubMed
    5. El-Elimat T. Figueroa M. Raja A. H. Graf T. N. Swanson S. M. Falkinham III J. O. Wani M. C. Pearce C. J. Oberlies N. H. Eur. J. Org. Chem. 2015:109. doi: 10.1002/ejoc.201402984. - DOI - PMC - PubMed
    6. Yodsing N. Lekphrom R. Sangsopha W. Aimi T. Boonlue S. Curr. Microbiol. 2018;75:513. doi: 10.1007/s00284-017-1411-y. - DOI - PubMed
    7. Xie L. Li M. Liu D. Wang X. Wang P. Dai H. Yang W. Liu W. Hu X. Zhao M. Molecules. 2019;24:393. doi: 10.3390/molecules24030393. - DOI - PMC - PubMed
    1. Bröhmer M. C. Bourcet E. Nieger M. Bräse S. Chem.–Eur. J. 2011;17:13706. doi: 10.1002/chem.201102192. - DOI - PubMed
    2. Masters K. S. Bräse S. Chem. Rev. 2012;112:3717. doi: 10.1021/cr100446h. - DOI - PubMed
    3. Tietze L. F. Ma L. Reiner J. R. Jackenkroll S. Heidemann S. Chem.–Eur. J. 2013;19:8610. doi: 10.1002/chem.201300479. - DOI - PubMed
    4. Sudhakar G. Bayya S. Kadam V. D. Nanubolu J. B. Org. Biomol. Chem. 2014;12:5601. doi: 10.1039/C4OB00950A. - DOI - PubMed
    5. Adachi K. Hasegawa S. Katakawa K. Kumamoto T. Tetrahedron Lett. 2017;58:4479. doi: 10.1016/j.tetlet.2017.10.038. - DOI
    1. Qin T. Johnson R. P. Porco Jr J. A. J. Am. Chem. Soc. 2011;133:1714. doi: 10.1021/ja110698n. - DOI - PMC - PubMed
    1. Qin T. Porco Jr J. A. Angew. Chem. 2014;126:3171. doi: 10.1002/ange.201311260. - DOI
    2. Qin T. Skraba-Joiner S. L. Khalil Z. G. Johnson R. P. Capon R. J. Porco Jr J. A. Nat. Chem. 2015;7:234. doi: 10.1038/nchem.2173. - DOI - PMC - PubMed
    3. Qin T. Iwata T. Ransom T. T. Beutler J. A. Porco Jr J. A. J. Am. Chem. Soc. 2015;137:15225. doi: 10.1021/jacs.5b09825. - DOI - PMC - PubMed
    4. Wu X. W. Iwata T. Scharf A. Qin T. Reichl K. D. Porco Jr J. A. J. Am. Chem. Soc. 2018;140:5969. doi: 10.1021/jacs.8b02535. - DOI - PMC - PubMed
    1. Stubbing L. A. Li F. F. Furkert D. P. Caprio V. E. Brimble M. A. Tetrahedron. 2012;68:6948. doi: 10.1016/j.tet.2012.05.115. - DOI
    2. Liu J. Li Z. Tong P. Xie Z. Zhang Y. Li Y. J. Org. Chem. 2015;80:1632. doi: 10.1021/jo502571r. - DOI - PubMed