Synfacts 2008(3): 0229-0229  
DOI: 10.1055/s-2008-1042655
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of ()-γ-Rubromycin

Contributor(s): Philip Kocienski, Zofia Komsta
S. Akai, K. Kakiguchi, Y. Nakamura, I. Kuriwaki, T. Dohi, S. Harada, O. Kubo, N. Morita, Y. Kita*
Osaka University, Japan
Further Information

Publication History

Publication Date:
21 February 2008 (online)

Significance

γ-Rubromycin is a red pigment isolated from a strain of Streptomyces collinus along with β-rubromycin. Both metabolites show some antimicrobial properties. They inhibit the reverse transcriptase of HIV-1 and human telomerase enzyme at micromolar IC50 values. The synthesis focuses on two aromatic Pummerer reactions to create first the spiroketal C and then the o-qui­none D.