Journal
TETRAHEDRON LETTERS
Volume 52, Issue 9, Pages 983-986Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.12.061
Keywords
K1115 B-1; Alnumycin; BE-41956A; Total synthesis; Structural determination; Michael-Dieckmann type condensation
Categories
Funding
- GCOE program 'Center for Practical Chemical Wisdom'
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
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K1115 B-1, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B-1 by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of H-1 NMR spectra and optical rotations made it clear that the absolute structures of K1115 B-1 alpha (the major isomer) and K1115 B-1 beta (the minor isomer) were (1R,17S)- and (1R, 17R)-configurations, respectively. The optical rotations of the stereoisomers revealed that alnumycin, reported as the identical structure with K1115 B-1, might be another mixture of stereoisomers. (C) 2010 Elsevier Ltd. All rights reserved.
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