The first total synthesis and structural determination of antibiotics K1115 B 1 s (alnumycins)

K Tatsuta, S Tokishita, T Fukuda, T Kano, T Komiya…

Index: Tatsuta, Kuniaki; Tokishita, Sonoko; Fukuda, Tomohiro; Kano, Takaaki; Komiya, Tadaaki; Hosokawa, Seijiro Tetrahedron Letters, 2011 , vol. 52, # 9 p. 983 - 986

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Citation Number: 14

Abstract

K1115 B1, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B1 by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of 1H NMR spectra and optical rotations made it clear that the absolute structures of K1115 B1α (the major isomer) and K1115 B1β (the minor isomer) were (1R, 17S)-and (1R, 17R)- ...