Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis

The first total synthesis of extracellular factor, “Avenolide”, in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the...

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Veröffentlicht in:	Journal of antibiotics 2011-12, Vol.64 (12), p.781-787
Hauptverfasser:	Uchida, Miho, Takamatsu, Satoshi, Arima, Shiho, Miyamoto, Kiyoko T, Kitani, Shigeru, Nihira, Takuya, Ikeda, Haruo, Nagamitsu, Tohru
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Butyrolactone - analogs & derivatives 4-Butyrolactone - biosynthesis 4-Butyrolactone - chemical synthesis 4-Butyrolactone - chemistry 4-Butyrolactone - metabolism 631/1647/2258 631/326/22 631/326/41 631/92/60 Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Life Sciences Magnetic Resonance Spectroscopy Medicinal Chemistry Microbiology Organic Chemistry original-article Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Infrared Stereoisomerism Streptomyces - chemistry Streptomyces - metabolism Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	The first total synthesis of extracellular factor, “Avenolide”, in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the absolute configuration of avenolide as 4 S ,10 R , and yielded important information on its structure–activity relationship.
ISSN:	0021-8820 1881-1469
DOI:	10.1038/ja.2011.90