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
. 2014 Jan 3;16(1):94-7.
doi: 10.1021/ol403078e. Epub 2013 Dec 6.

Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs

Hanmo Zhang  1 , Kyu Ok Jeon, E Ben Hay, Steven J Geib, Dennis P Curran, Matthew G LaPorte
Affiliations

Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs

Hanmo Zhang et al. Org Lett. .

Abstract

A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Structures of meloscine 1a, epimeloscine 2s, and scandine 3.
Figure 2
Figure 2
Fragments in the design of the pentacyclic analogs
Figure 3
Figure 3
ORTEP structure of amine 18b.
Scheme 1
Scheme 1
Divinylcyclopropane cascade cyclization with likely intermediates.
Scheme 2
Scheme 2
Synthesis of annulation precursors 16a–c.
Scheme 3
Scheme 3
Completion of the D-ring analog synthesis. a) crude product used directly in the next step; b) two-step yield
Scheme 4
Scheme 4
Synthesis of E-ring analogs.
Scheme 5
Scheme 5
Synthesis of substituted B-ring analogs.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Huryn DM, Wipf P. Natural Product Chemistry and Cancer Drug Discovery, 2nd Edition. In: Neidle S, editor. Cancer Drug Discovery. Academic Press; 2013. pp. 91–120. Part II.
    2. Ganesan A. Curr. Opin. Chem. Biol. 2008;12:306–317. - PubMed
    3. Newman DJ, Cragg GM. J. Nat. Prod. 2012;75:311–335. - PMC - PubMed
    1. Clemons PA, Wilson JA, Dančik V, Muller S, Carrinski HA, Wagner BK, Koehler AN, Schreiber SL. Proc. Natl. Acad. Sci. U.S.A. 2011;108:6817–6822. - PMC - PubMed
    2. Clemons PA, Bodycombe NE, Carrinski HA, Wilson JA, Shamji AF, Wagner BK, Koehler AN, Schreiber SL. Proc. Natl. Acad. Sci. U.S.A. 2010;107:18787–18792. - PMC - PubMed
    3. Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009;52:6752–6756. - PubMed
    4. Camp D, Davis RA, Campitelli M, Ebdon J, Quinn RJ. J. Nat. Prod. 2012;75:72–81. - PubMed

    1. (a) Isolation: Bernauer K, Englert G, Vetter W, Weiss E. Helv. Chim. Acta. 1969;52:1886–1905. (b) Short review: Szabó LF. Arkivoc. 2007;7:280–290.

    1. Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008;41:40–49. - PubMed
    2. Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007;107:3117–3179. - PubMed
    1. Trost BM, Morris PJ, Sprague SJ. J. Am. Chem. Soc. 2012;134:17823–17831. - PMC - PubMed

Publication types

MeSH terms

LinkOut - more resources