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 Jun 8;8(12):2643-5.
doi: 10.1021/ol0608799.

An approach to the total synthesis of welwistatin

Thomas J Greshock  1 , Raymond L Funk
Affiliations

An approach to the total synthesis of welwistatin

Thomas J Greshock et al. Org Lett. .

Abstract

An approach to the total synthesis of the antimicrotubule agent welwistatin is described. Key transformations include (1) a 7-endo intramolecular conjugate addition reaction of enone 6 to deliver the strained bicyclo[4.3.1]decanone 5; (2) a 6pi electrocyclic ring closure of trienecarbamate 16 followed by oxidation to afford protected aniline 17; and (3) an intramolecular cyclization of acetic acid derivative 18 to give rise to indole 19. [reaction: see text]

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

References

    1. Smith CD, Zilfou JT, Stratmann K, Patterson G, Moore RE. Mol. Pharm. 1995;47:241. - PubMed
    2. Zhang X, Smith CD. Mol. Pharm. 1996;49:288. - PubMed
    1. Smith CD, Zilfou JT, Stratmann K, Patterson G, Moore RE. Mol. Pharm. 1995;47:241. - PubMed
    2. Zhang X, Smith CD. Mol. Pharm. 1996;49:288. - PubMed

    1. For approaches to the welwitindolinones, seeKonopelski JP, Deng H, Schiemann K, Keane JM, Olmstead MM. Synlett. 1998:1105.Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J. Am. Chem. Soc. 1999;121:6326.Kaoudi T, Quiclet-Sire B, Seguin S, Zard SZ. Angew. Chem. Int. Ed. 2000;39:731.Konopelski JP, Deng H. Org. Lett. 2001;3:3001.Jung ME, Slowinski F. Tetrahedron Lett. 2001;42:6835.López-Alvarado P, García-Granda S, Álvarez-Rúa C. Eur. J. Org. Chem. 2002:1702.Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew. Chem. Int. Ed. 2004;43:1270.MacKay JA, Bishop RL, Rawal VH. Org. Lett. 2005;7:3421.Baudoux J, Blake AJ, Simpkins NS. Org. Lett. 2005;7:4087.(j) For a review, seeAvendano C, Menéndez JC. Curr. Org. Syn. 2004;1:65.

    1. For total syntheses of welwitindolinone A, seeBaran PS, Richter JM. J. Am. Chem. Soc. 2005;127:15394.Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J. Am. Chem. Soc. 2006 ASAP.

    1. Greshock TJ, Funk RL. J. Am. Chem. Soc. 2002;124:754. - PubMed

Publication types