Isolation of lomaiviticins C-E, transformation of lomaiviticin C to lomaiviticin A, complete structure elucidation of lomaiviticin A, and structure-activity analyses

Christina M Woo; Nina E Beizer; Jeffrey E Janso; Seth B Herzon

doi:10.1021/ja3074984

Isolation of lomaiviticins C-E, transformation of lomaiviticin C to lomaiviticin A, complete structure elucidation of lomaiviticin A, and structure-activity analyses

J Am Chem Soc. 2012 Sep 19;134(37):15285-8. doi: 10.1021/ja3074984. Epub 2012 Sep 10.

Authors

Christina M Woo¹, Nina E Beizer, Jeffrey E Janso, Seth B Herzon

Affiliation

¹ Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

PMID: 22963534
DOI: 10.1021/ja3074984

Abstract

We describe the isolation of (-)-lomaiviticins C-E (6-8), elucidation of the complete absolute and relative stereochemistry of (-)-lomaiviticin A (1), the synthetic conversion of (-)-lomaiviticin C (6) to (-)-lomaiviticin A (1), and the first evidence that the dimeric diazofluorene of (-)-lomaiviticin A (1) plays a defining and critical role in antiproliferative activity.

Publication types

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

MeSH terms

Fluorenes / chemistry
Fluorenes / isolation & purification*
Magnetic Resonance Spectroscopy
Molecular Structure
Structure-Activity Relationship

Substances

Fluorenes