Synthesis of (—)‐Malyngolide | Zendy

Flörke Holger | Zendy; Schaumann Ernst | Zendy

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Synthesis of (—)‐Malyngolide

Author(s) -

Flörke Holger,

Schaumann Ernst

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960124

Subject(s) - chemistry , epoxide , propargyl , acetal , triple bond , derivative (finance) , optically active , catalysis , combinatorial chemistry , natural product , medicinal chemistry , ring (chemistry) , stereochemistry , double bond , organic chemistry , financial economics , economics

δ‐Lactone (–)‐malyngolide ( 1 ) was synthesized by starting from the optically active epoxide 5 . Coupling of derivative 3 with propargyl anion 11 and subsequent metal‐catalyzed methylation of the triple bond provided 14 incorporating all the carbon atoms of 1 . Cyclization to the acetal 16 was achieved via the epoxidation product 15 . Adjustment of the oxidation state and removal of protective groups complete the synthesis of 1 .

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