Chemistry and structural determination of botcinolides, botcinins, and botcinic acids
Literature Information
Publication Date
2008-12-03
DOI
10.1039/B814375G
Impact Factor
6.222
Authors
Isamu Shiina, Hiroki Fukui
View Original
Abstract
The first asymmetric total syntheses of botcinins C (18), D (19), E (20), and F (21), botcinic acid (22), botcinic acid methyl ester (23), botcineric acid (26), and 3-O-acetylbotcinic acid methyl ester (27) were achieved. The structures of these compounds have been unequivocally determined through their total syntheses and those of 20, 22, 23, 26, and 27 are identified with the revised forms of the natural products formerly assumed to be 2-epibotcinolide (10), botcinolide (6), 4-O-methylbotcinolide (7), homobotcinolide (11), and 3-O-acetyl-5-O-methylbotcinolide (8), respectively. It was further proved that the proposed nine-membered ring structure of 2-epibotcinolide (10) is very unstable and the ineluctable translactonization easily occurred to form the corresponding γ-lactone57.
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Source Journal
Chemical Communications
CiteScore:
8.6
Self-citation Rate:
4.7%
Articles per Year:
2458
ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry
Recommended Compounds
![4-Fluoro-2-(4-{[(3S,4R)-4-(2-hydroxy-2-propanyl)-3-pyrrolidinyl]amino}-6,7-dimethoxy-2-quinazolinyl)phenol hydrochloride (1:1) structure](https://static.chemtradehub.com/structs/143/1431697-96-9-619c.webp "4-Fluoro-2-(4-{[(3S,4R)-4-(2-hydroxy-2-propanyl)-3-pyrrolidinyl]amino}-6,7-dimethoxy-2-quinazolinyl)phenol hydrochloride (1:1) structure")
4-Fluoro-2-(4-{[(3S,4R)-4-(2-hydroxy-2-propanyl)-3-pyrrolidinyl]amino}-6,7-dimethoxy-2-quinazolinyl)phenol hydrochloride (1:1)
CAS Number:
1431697-96-9
Molecular Formula:
C23H28ClFN4O4
![[3-Fluoro-4-(1-pyrrolidinylcarbonyl)phenyl]boronic acid structure](https://static.chemtradehub.com/structs/874/874289-09-5-e3d4.webp "[3-Fluoro-4-(1-pyrrolidinylcarbonyl)phenyl]boronic acid structure")
[3-Fluoro-4-(1-pyrrolidinylcarbonyl)phenyl]boronic acid
CAS Number:
874289-09-5
Molecular Formula:
C11H13BFNO3
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