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
. 2008 Apr 3;10(7):1421-4.
doi: 10.1021/ol8001865. Epub 2008 Mar 7.

A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D

Alan Whitehead  1 , Joshua D Waetzig, Christopher D Thomas, Paul R Hanson
Affiliations

A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D

Alan Whitehead et al. Org Lett. .

Abstract

Construction of the C15-C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Retrosynthetic Analysis of Dolabelide C
Scheme 2
Scheme 2
Synthesis of Aldehyde 11
Scheme 3
Scheme 3
Asymmetric Vinylate Additions into 11a/11b
Scheme 4
Scheme 4
Construction of Alcohol 14b
Scheme 5
Scheme 5
Completion of the C15-C30 Subunit of Dolabelide
Scheme 6
Scheme 6
CM Route to the C15-C30 Subunit of Dolabelide
See this image and copyright information in PMC

References

    1. Ojika M, Nagoya T, Yamada K. Tetrahedron Lett. 1995;36:7491–7494.
    1. Suenaga K, Nagoya T, Shibata T, Kigoshi H, Yamada K. J. Nat. Prod. 1997;60:155–157.
    1. Grimaud L, Rotulo D, Ros-Perez R, Guitry-Azam L, Prunet J. Tetrahedron Lett. 2002;43:7477–7479.
    2. Grimaud L, deMesmay R, Prunet J. Org. Lett. 2002;4:419–421. - PubMed
    3. Desroy N, Le Roux R, Phansavath P, Chiummiento L, Bonini C, Genêt J-P. Tetrahedron Lett. 2003;44:1763–1766.
    4. Schmidt DR, Park PK, Leighton JL. Org. Lett. 2003;5:3535–3537. - PubMed
    5. Le Roux R, Desroy N, Phansavath P, Genêt J-P. Synlett. 2005:429–432.
    6. Keck GE, McLaws MD. Tetrahedron Lett. 2005;46:4911–4914. - PMC - PubMed
    7. Vincent A, Prunet J. Synlett. 2006:2269–2271.
    1. Park PK, O’Malley SJ, Schmidt DR, Leighton JL. J. Am. Chem. Soc. 2006;128:2796–2797. - PMC - PubMed
    1. Whitehead A, McReynolds MD, Moore JD, Hanson PR. Org. Lett. 2005;7:3375–3378. - PubMed
    2. Whitehead A, McParland JP, Hanson PR. Org. Lett. 2006;8:5025–5028. - PubMed
    3. Waetzig JD, Hanson PR. Org. Lett. 2006;8:1673–1676. - PubMed

Publication types