Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 9, Pages 2783-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja7113757
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- NHLBI NIH HHS [HL25848] Funding Source: Medline
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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.
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