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New Stereospecific Synthetic Routes to the Bicyclo[3.2.1]octane Subunit of the Kaurenoids and Gibberellins

✍ Scribed by E.J Corey; Kun Liu

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 452 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01798-x

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✦ Synopsis

Three new sequences are described for the synthesis of the bicyclo [3.2.l]octane core of diterpenoiok such as the kaurenes (Schemes 1-3). 01997 Elsevier Science Ltd.

The tricyclic system 1 is a prominent feature of many naturally occurring diterpenoids, including kaurenoids and gibberellins (ent-kaurenoids). The biological importance and structural complexity of these natural products have stimulated an enormous body of research on their synthesis.l In connection with recent studies directed at the total synthesis of the potent anti-HIV kaurenoid neotripterifordin (3),2 we have developed new stereocontrolled processes for the construction of 1and also the trans-6/6-fused diastereomeric unit 2, which are described herein.

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