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An efficient total synthesis of the anticancer agent (+)-spisulosine (ES-285) from Garner’s aldehyde

✍ Scribed by Partha Ghosal; Arun K. Shaw

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
254 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient total synthesis of (+)-spisulosine (ES-285) was completed in nine steps from (S)-Garner's aldehyde. The vicinal amino alcohol moiety with anti-configuration was achieved by a highly diastereoselective addition of vinyl magnesium bromide to Garner's aldehyde. The long hydrocarbon chain of the antitumor natural product was installed via olefin cross metathesis of the benzyl-protected allylic alcohol with an appropriate olefin counterpart followed by hydrogenation.

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