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Stereospecific synthesis of exo-allylic alcohol. An efficient asymmetric synthesis of (R)-(-)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthols

✍ Scribed by Mikiko Sodeoka; Takamasa Iimori; Masakatsu Shibasaki

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 264 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99036-1

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✦ Synopsis

A method for the stereospecific synthesis of exo-allylic alcohols with trisubstituents is described. Using this methodology in combination with Sharpless catalytic asymmetric epoxidation, an efficient synthesis of (RI-(-)-2-acetyl-5,8-dimethoxy-1,2,3,4tetrahydro-2-naphthol ( 5). an important intermediate for the anthracycline synthesis, has been accomplished in 36% overall yield from 5.8-dimethoxy-2-tetralone ( 6) with 93% e.e.. 1) and 4-demethoxydaunorubicin (2) are expected to be more clinically useful antineoplastic agents than naturally occurring anthracyclines 3 and 4.2

4-Demethoxyadriamycin (

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