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Synthesis 2009(8): 1386-1392  
DOI: 10.1055/s-0028-1087993
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Kommu Nagaiah*, Domalapally Sreenu, Kamaraju V. Purnima, Ramisetti Srinivasa Rao, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: nagaiah@iict.res.in;
Further Information

Publication History

Received 3 December 2008
Publication Date:
06 March 2009 (online)

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Abstract

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.

Key words

d-mannitol - allylation - Grignard reaction - ring-closing metathesis - Michael addition

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