Total synthesis and structural revision of viridicatumtoxin B

K C Nicolaou; Christian Nilewski; Christopher R H Hale; Heraklidia A Ioannidou; Abdelatif ElMarrouni; Lizanne G Koch

doi:10.1002/anie.201304691

Total synthesis and structural revision of viridicatumtoxin B

Angew Chem Int Ed Engl. 2013 Aug 12;52(33):8736-41. doi: 10.1002/anie.201304691. Epub 2013 Jul 24.

Authors

K C Nicolaou¹, Christian Nilewski, Christopher R H Hale, Heraklidia A Ioannidou, Abdelatif ElMarrouni, Lizanne G Koch

Affiliation

¹ Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. kcn@rice.edu

Abstract

Will the real viridicatumtoxin B please stand up: Total synthesis of viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule.

Keywords: antibiotics; natural products; structural revision; tetracyclines; total synthesis.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Models, Chemical
Molecular Structure
Mycotoxins / chemistry*
Spiro Compounds / chemistry*
Tetracycline / chemistry*
Tetracyclines / chemical synthesis*
Tetracyclines / chemistry*

Substances

Mycotoxins
Spiro Compounds
Tetracyclines
spirohexaline
viridicatumtoxin B
Tetracycline

Abstract

Publication types

MeSH terms

Substances

Grants and funding