A concise asymmetric synthesis of 5,8-disubstituted indolizidine alkaloids. Total synthesis of (−)-indolizidine 209B

A general access to 5,8-disubstituted indolizidine alkaloids has been developed, where the asymmetric addition of an optically active allenyltitanium to benzyl[4-( tert-butyldimethylsilyloxy)butylidene]amine ( 2 ) is the key reaction. As a typical example, (−)-indolizidine 209B was efficiently synth...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 48; pp. 8635 - 8637
Main Authors Song, Yongcheng, Okamoto, Sentaro, Sato, Fumie
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.11.2002
Elsevier
Subjects
asymmetric addition
Chemistry
Chemistry, Organic
chiral allenyltitanium
imine
indolizidine alkaloid
Physical Sciences
Science & Technology
indolizidine alkaloid
asymmetric addition
chiral allenyltitanium
imine
REAGENT
PIPERIDINE
AXIAL CHIRALITY
OPTICALLY-ACTIVE ALLENYLTITANIUMS
PYRROLES
ALKYNES
QUINOLIZIDINES
EFFICIENT
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Summary:A general access to 5,8-disubstituted indolizidine alkaloids has been developed, where the asymmetric addition of an optically active allenyltitanium to benzyl[4-( tert-butyldimethylsilyloxy)butylidene]amine ( 2 ) is the key reaction. As a typical example, (−)-indolizidine 209B was efficiently synthesized in 40% overall yield in a five-step reaction starting from readily available ( S)-1-methyl-3-trimethylsilylprop-2-ynyl phosphate ( 1 ). Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02149-4