Asymmetric synthesis of (-)-leiocarpin A via (-)-(S)-goniothalamin employing Julia-Kocienski olefination

A concise and enantioselective syntheses of antileukemic natural products such as (-)-(S)-goniothalamin and (-)-leiocarpin A has been accomplished in excellent yields. By employing reported conditions on suitable substrates via Julia-Kocienski olefination, intramolecular lactonization, and subsequen...

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Bibliographic Details
Published in:Synthetic communications 2016-01, Vol.46 (2), p.187-196
Main Authors: Meruva, Suresh Babu, Rao K., Raghavendra, Mohammed, Aaseef, Dahanukar, Vilas H., Kumar, U. K. Syam, Dubey, P. K.
Format: Article
Language:English
Subjects:
Acetonide deprotection
Julia-Kocienski olefination
lactonization
Michael addition
saturated and unsaturated pyranone
sharpless asymmetric dihydroxylation
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Summary:A concise and enantioselective syntheses of antileukemic natural products such as (-)-(S)-goniothalamin and (-)-leiocarpin A has been accomplished in excellent yields. By employing reported conditions on suitable substrates via Julia-Kocienski olefination, intramolecular lactonization, and subsequently dehydroxylative olefination, (-)-(S)-goniothalamin was synthesized. Then Sharpless asymmetric dihydroxylation-intramolecular Michael addition on (-)-(S)-goniothalamin provided (-)-leiocarpin A.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2015.1128546