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A novel antileukemic sesquiterpene lactone. Synthesis of racemic eriolanin

✍ Scribed by Takeshi Wakamatsu; Nobuhide Miyachi; Fumihiro Ozaki; Masakatsu Shibasaki; Yoshio Ban

Book ID
104217568
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
240 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of dl-errolantn 1, htghly oxygenated IJO-secoeudesmanollde rsolated from the chloroform extracts of Erronhvllum Forbes (Composltae), as reported , 95% , c MeUNaHITHF, 92% , d CI,CCOCl /Zn-C&thcr/ri,S 5hr ; c ZnlNH,CIIMeOHIOΒ°C, 44% from 10 , 1 PhSNa!MeOH/rl, 74% ; g NaBE,/MeOH, quant , b MsClIPy, quant. , i t-BuOWDMSO, 81% , j H&$1, ICH,CN-If,00 1)/40Β°C,89% Me OAc Me OAc Me 6Ac 19 20a 20b

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A total synthesis of racemic eriolanin
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## Abstract Using a sultone as the key intermediate, the first enantioselective total synthesis of the antileukemic 1,10‐__seco__‐eudesmanolides (–)‐eriolanin (**1**) and (–)‐eriolangin (**2**) was achieved, which also established the hitherto unknown absolute configuration of these sesquiterpene l