A direct route to fluostatin C by a fascinating Diels-Alder reaction.
The Diels-Alder reactions between vinylindenes (5 or 6) as the dienes with quinoneketals (7 or 8) or with methacrolein as the dienophiles were investigated. The remarkable regioselectivities of these Diels-Alder adducts suggested that the regiopreferences of these dienes and dienophiles in these cases are not a fixed property of each component of the cycloaddition but are mutually contigent. This paper shows how the Diels-Alder reaction between 6 and 8 was applied to the inaugural total syntheses of fluostatin C and E.
Yu
Maolin
M
Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA.
Danishefsky
Samuel J
SJ
D000466:Alkadienes / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D005449:Fluorenes; D011809:Quinones; C512873:fluostatin C