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 |
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| container_end_page | 787 |
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| container_issue | 12 |
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| container_title | Journal of antibiotics |
| container_volume | 64 |
| creator | Uchida, Miho Takamatsu, Satoshi Arima, Shiho Miyamoto, Kiyoko T Kitani, Shigeru Nihira, Takuya Ikeda, Haruo Nagamitsu, Tohru |
| description | 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. |
| doi_str_mv | 10.1038/ja.2011.90 |
| format | Article |
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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
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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.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - biosynthesis</subject><subject>4-Butyrolactone - chemical synthesis</subject><subject>4-Butyrolactone - chemistry</subject><subject>4-Butyrolactone - metabolism</subject><subject>631/1647/2258</subject><subject>631/326/22</subject><subject>631/326/41</subject><subject>631/92/60</subject><subject>Bacteriology</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medicinal Chemistry</subject><subject>Microbiology</subject><subject>Organic Chemistry</subject><subject>original-article</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Infrared</subject><subject>Stereoisomerism</subject><subject>Streptomyces - chemistry</subject><subject>Streptomyces - 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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.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>21989459</pmid><doi>10.1038/ja.2011.90</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of antibiotics, 2011-12, Vol.64 (12), p.781-787 |
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| language | eng |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Alma/SFX Local Collection |
| subjects | 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 |
| title | Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis |
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