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First stereoselective synthesis of synargentolide A and revision of absolute stereochemistry

✍ Scribed by Gowravaram Sabitha; Peddabuddi Gopal; C. Nagendra Reddy; J.S. Yadav

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
337 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first stereoselective total synthesis of synargentolide A isolated from Syncolostemon argenteus has been achieved from commercially available (R)-benzyl glycidyl ether using Sharpless asymmetric epoxidation and cross-metathesis reactions as the key steps. Comparing the spectral data of the synthesized and naturally occurring synargentolide A, the C4 0 and C6 0 -stereogenic centers of the natural synargentolide A were assigned a corrected anti relationship.

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