An enantio- and diastereoselective synthesis of (-)-isoretronecanol and (+)-trachelanthamidine from a meso precursor

Two diastereomeric pyrrolizidine alkaloids, (-)-isoretronecanol and (+)-trachelanthamidine, have been synthesized in an enantio- and diastereoselective manner starting from a meso precursor via a catalytic asymmetrization.

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Bibliographic Details
Published inHeterocycles Vol. 49; pp. 33 - 37
Main Authors Konno, H, Kishi, M, Hiroya, K, Ogasawara, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 31.12.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BASES
ASYMMETRIC-SYNTHESIS
BICYCLIC ALKALOIDS
PYRROLIZIDINE ALKALOIDS
ENANTIOCONTROLLED SYNTHESIS
RADICAL CYCLIZATION
(-)-SUPINIDINE
ATOM RING JUNCTURE
CLAISEN REARRANGEMENT
(-)-TRACHELANTHAMIDINE
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Summary:Two diastereomeric pyrrolizidine alkaloids, (-)-isoretronecanol and (+)-trachelanthamidine, have been synthesized in an enantio- and diastereoselective manner starting from a meso precursor via a catalytic asymmetrization.
ISSN:0385-5414
DOI:10.3987/com-97-s4