Asymmetric Synthesis via Heterocyclic Intermediates, XLVII. Asymmetric Synthesis of (+)‐(1 R ,2 S )‐ allo ‐Coronamic Acid | Zendy

Groth Ulrich | Zendy; Halfbrodt Wolfgang | Zendy; Schöllkopf Ulrich | Zendy

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Asymmetric Synthesis via Heterocyclic Intermediates, XLVII. Asymmetric Synthesis of (+)‐(1 R ,2 S )‐ allo ‐Coronamic Acid

Author(s) -

Groth Ulrich,

Halfbrodt Wolfgang,

Schöllkopf Ulrich

Publication year - 1992

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.199219920162

Subject(s) - chemistry , yield (engineering) , alkylation , intramolecular force , lithium (medication) , allylic rearrangement , tsuji–trost reaction , stereochemistry , chloride , medicinal chemistry , organic chemistry , catalysis , medicine , materials science , metallurgy , endocrinology

allo ‐Coronamic acid ( 1 ) was synthesized in five steps enantiomerically and diastereomerically virtually pure by starting from the bislactim ethers of cyclo(‐ L ‐Val‐Gly‐) ( 3a ) or cyclo‐(‐ L ‐ tert ‐Leu‐Gly‐) ( 3b ) in an overall yield of 31%. The key step of this synthesis is the intramolecular alkylation of the lithium azaenolate derived from the allylic chloride 4 .

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