Stereoselective Total Syntheses of Leiocarpin A and (-)-Galantinic Acid Starting from D-Mannitol

Stereoselective total syntheses of leiocarpin A and (-)-galantinic acid, starting from D-mannitol as a chiral synthon, are described. The key steps involve stereoselective allylations, a Grignard reaction to control the required stereogenic centers, and ring-closing metathesis followed by intramolec...

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Published inSynthesis (Stuttgart) no. 8; pp. 1386 - 1392
Main Authors Nagaiah, Kommu, Sreenu, Domalapally, Purnima, Kamaraju V., Rao, Ramisetti Srinivasa, Yadav, Jhillu S.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.04.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
EFFICIENT TOTAL-SYNTHESIS
GALANTINIC ACID
(+)-8-ACETYLGONIOTRIOL
ring-closing metathesis
1ST ENANTIOSELECTIVE SYNTHESIS
(+)-9-DEOXYGONIOPYPYRONE
STYRYL-LACTONES
Grignard reaction
(+)-ALTHOLACTONE
STYRYLLACTONE (+)-GONIODIOL
allylation
CYTOTOXICITY
GONIOTHALAMIN
D-mannitol
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Summary:Stereoselective total syntheses of leiocarpin A and (-)-galantinic acid, starting from D-mannitol as a chiral synthon, are described. The key steps involve stereoselective allylations, a Grignard reaction to control the required stereogenic centers, and ring-closing metathesis followed by intramolecular Michael addition.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0028-1087993