Enantiospecific total synthesis of indole alkaloids (+)-eburnamonine, (−)-aspidospermidine and (−)-quebrachamine

An enantiospecific total synthesis of indole alkaloids eburnamonine, aspidospermidine and quebrachamine is described from lactic acid. Synthesis of all three alkaloids is accomplished from a single chiral building block. Johnson–Claisen rearrangement of a chiral allyl alcohol is the main feature for...

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Bibliographic Details
Published in:Tetrahedron 2013-07, Vol.69 (26), p.5525-5536
Main Authors: Nidhiry, John Eugene, Prasad, Kavirayani R.
Format: Article
Language:English
Subjects:
Alcohols
Alkaloids
Claisen rearrangement
Enantiospecific synthesis
Indole alkaloids
Indoles
Lactic acid
Synthesis
Tetrahedrons
Total synthesis
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Summary:An enantiospecific total synthesis of indole alkaloids eburnamonine, aspidospermidine and quebrachamine is described from lactic acid. Synthesis of all three alkaloids is accomplished from a single chiral building block. Johnson–Claisen rearrangement of a chiral allyl alcohol is the main feature for the installation of the required quaternary centre. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.04.097