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 B 1α (the major isomer) and K1115 B1β (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 B1, might be another mixture of stereoisomers.
Original language | English |
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Pages (from-to) | 983-986 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 52 |
Issue number | 9 |
DOIs | |
Publication status | Published - 2011 Mar 2 |
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Keywords
- Alnumycin
- BE-41956A
- K1115 B
- Michael-Dieckmann type condensation
- Structural determination
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins). / Tatsuta, Kuniaki; Tokishita, Sonoko; Fukuda, Tomohiro; Kano, Takaaki; Komiya, Tadaaki; Hosokawa, Seijiro.
In: Tetrahedron Letters, Vol. 52, No. 9, 02.03.2011, p. 983-986.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)
AU - Tatsuta, Kuniaki
AU - Tokishita, Sonoko
AU - Fukuda, Tomohiro
AU - Kano, Takaaki
AU - Komiya, Tadaaki
AU - Hosokawa, Seijiro
PY - 2011/3/2
Y1 - 2011/3/2
N2 - 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 B 1α (the major isomer) and K1115 B1β (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 B1, might be another mixture of stereoisomers.
AB - 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 B 1α (the major isomer) and K1115 B1β (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 B1, might be another mixture of stereoisomers.
KW - Alnumycin
KW - BE-41956A
KW - K1115 B
KW - Michael-Dieckmann type condensation
KW - Structural determination
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=79251597606&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79251597606&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2010.12.061
DO - 10.1016/j.tetlet.2010.12.061
M3 - Article
AN - SCOPUS:79251597606
VL - 52
SP - 983
EP - 986
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 9
ER -