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Toward the second-generation synthesis of zaragozic acids: Construction of the 2,8-dioxabicyclo[3.2.1]octane core system via tandem carbonyl ylide Formation and 1,3-dipolar cycloaddition sequence

✍ Scribed by Osamu Kataoka; Shinji Kitagaki; Nobuhide Watanabe; Jun-ichi Kobayashi; Sei-ichi Nakamura; Motoo Shiro; Shun-ichi Hashimoto

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 380 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00203-2

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✦ Synopsis

A highly eJicient construction of the 2,8-dioxabicyclo[l2,1]octane core structure of zaragozic acids, inhibitors of the enzyme squalene synthase, hns been achieved by exploiting the sequence of rhodium(II)-mediated intramolecular carbonyl ylide formation from an a-diazo ester and stereocontrolled I.3-dip&r cyclooddition with (El-3-hexene-2.5-dione.

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