The First Total Synthesis of (±)-Scopadulin, an Antiviral Aphidicolane Diterpene

The first total synthesis of (±)-scopadulin was accomplished by a stereoselective construction of a quaternary carbon at C-4, conversion of the hindered cyano group to a methyl group via our novel reaction for conversion of primary aliphatic amines into alcohols, and a highly chemo- and stereoselect...

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Published inOrganic letters Vol. 3; no. 4; pp. 619 - 621
Main Authors Rahman, S. M. Abdur, Ohno, Hiroaki, Murata, Takashi, Yoshino, Hitoshi, Satoh, Norifumi, Murakami, Kazuo, Patra, Debasis, Iwata, Chuzo, Maezaki, Naoyoshi, Tanaka, Tetsuaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.02.2001
Amer Chemical Soc
Subjects
Antiviral Agents - chemical synthesis
Chemistry
Chemistry, Organic
Diterpenes - chemical synthesis
Methylation
Molecular Structure
Physical Sciences
Plants, Medicinal - chemistry
Science & Technology
Stereoisomerism
Structure-Activity Relationship
STEMODANE DITERPENES
(+/-)-APHIDICOLIN
SCOPARIA-DULCIS L
CARBONYL-COMPOUNDS
ORGANOTITANIUM REAGENTS
ACID-A
(+/-)-STEMODINONE
FORMAL TOTAL SYNTHESIS
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Summary:The first total synthesis of (±)-scopadulin was accomplished by a stereoselective construction of a quaternary carbon at C-4, conversion of the hindered cyano group to a methyl group via our novel reaction for conversion of primary aliphatic amines into alcohols, and a highly chemo- and stereoselective methylation at C-16.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol007059v