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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 .