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
. 2006 Mar 2;8(5):903-6.
doi: 10.1021/ol0530225.

Progress toward the total synthesis of Bielschowskysin: a stereoselective [2+2] photocycloaddition

Brandon Doroh  1 , Gary A Sulikowski
Affiliations

Progress toward the total synthesis of Bielschowskysin: a stereoselective [2+2] photocycloaddition

Brandon Doroh et al. Org Lett. .

Abstract

The tetracyclic core of the diterpene bielschowskysin has been prepared as a single enantiomer via a stereoselective intramolecular [2+2] photocycloaddition of 5-alkylidene-2(5H)-furanone 3.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Structure of bielschowskysin.
Figure 2
Figure 2
Model for observed diastereoselectivity of [2+2] photocycloaddition.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
See this image and copyright information in PMC

References

    1. Review: Rodriquez AD. Tetrahedron. 1995;51:4571–4618.

    1. Look SA, Burch MT, Fenical W. J Org Chem. 1985;50:5741–5746.
    2. Marrero J, Rodriguez AD, Baran P, Raptis RG. J Org Chem. 2003;68:4977–4979. - PubMed
    3. Marrero J, Rodriguez AD, Baran P, Raptis RG. Org Lett. 2003;5:2551–2554. - PubMed
    4. Marrero J, Rodriguez AD, Baran P, Raptis RG. Eur J Org Chem. 2004:3909–3912.
    1. Marrero J, Rodriguez AD, Baran P, Raptis RG, Sánchez JA, Ortega-Barria E, Capson TL. Org Lett. 2004;6:1661–1664. - PubMed
    1. Brown GD, Wong HF. Tetrahedron. 2004;60:5439–5451.
    2. Gedge DR, Pattenden G, Smith AG. J Chem Soc Perkin Trans 1. 1986:2127–2131.
    1. Saito S, Hasegawa T, Inaba N, Nishida R, Fujii T, Nomizu S, Muriwake T. Chem Lett. 1984:1389–1392.

Publication types