Synthesis of southern (C1'-C11') and eastern (C8-C18) fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger

Synthesis of the southern C1'-C11' and eastern C8-C18 fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger, was achieved. The southern fragment was synthesized by using the Evans aldol reaction and cis-selective iodoetherification as the key steps in...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2001-12, Vol.65 (12), p.2630-2637
Main Authors: Kiyota, H. (Tohoku Univ., Sendai (Japan)), Furuya, Y, Kuwahara, S, Oritani, T
Format: Article
Language:English
Subjects:
aerial mycelium
antibiotic
ANTIBIOTICS
Biological and medical sciences
Biotechnology
CHEMICAL STRUCTURE
CHEMICAL SYNTHESIS
Fundamental and applied biological sciences. Psychology
Furans - chemistry
iodoetherification
Magnetic Resonance Spectroscopy
Molecular Structure
MYCELIUM
Mycelium - drug effects
pamamycin
Spectrometry, Mass, Fast Atom Bombardment
STREPTOMYCES
Streptomyces - chemistry
synthesis
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Summary:Synthesis of the southern C1'-C11' and eastern C8-C18 fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger, was achieved. The southern fragment was synthesized by using the Evans aldol reaction and cis-selective iodoetherification as the key steps in a 9.6% overall yield (7 steps). The eastern fragment was constructed via the Julia coupling reaction and cis-selective iodoetherification in a 3.0% overall yield (8 steps from the known epoxide).
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.65.2630