Stereoselective Total Synthesis of the Proposed Structure of 2-Epibotcinolide

The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing β-hydroxy ester units. Second, t...

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Published inOrganic letters Vol. 8; no. 23; pp. 5279 - 5282
Main Authors Shiina, Isamu, Takasuna, Yu-ji, Suzuki, Ryo-suke, Oshiumi, Hiromi, Komiyama, Yuri, Hitomi, Seiichi, Fukui, Hiroki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.11.2006
Amer Chemical Soc
Subjects
Botrytis - metabolism
Chemistry
Chemistry, Organic
Cyclization
Decanoates - chemical synthesis
Decanoates - metabolism
Lactones - chemical synthesis
Lactones - metabolism
Molecular Structure
Physical Sciences
Pyrones - chemical synthesis
Pyrones - metabolism
Science & Technology
BENZOIC ANHYDRIDES
ASYMMETRIC ALDOL REACTION
OCTALACTIN
METABOLITES
BOTRYTIS-CINEREA
SILYL ENOL ETHERS
CARBOXYLIC ESTERS
ALDEHYDES
LACTONIZATION
BOTCINOLIDE
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Summary:The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing β-hydroxy ester units. Second, the key cyclization reaction to form the nine-membered lactone moiety is efficiently achieved by the extremely facile and powerful mixed-anhydride method promoted by 2-methyl-6-nitrobenzoic anhydride (MNBA) with basic promoters.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062058+