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Stereoselective Total Synthesis of Stagonolide C

✍ Scribed by Jhillu S. Yadav; Nimmakayala Mallikarjuna Reddy; N. Venkateswar Rao; Md. Ataur Rahman; Attaluri R. Prasad

Book ID
102258562
Publisher
John Wiley and Sons
Year
2012
Tongue
German
Weight
199 KB
Volume
95
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A convergent and efficient total synthesis of stagonolide C (1), a phytotoxic metabolite, was achieved (Schemes 2 and 3) The synthesis exploited the high configuration control in the Prins cyclization along with alkene rearrangement and ring‐closing metathesis as key steps.

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## Abstract A simple asymmetric total synthesis of stagonolide G (**1**) is described. Asymmetric dihydroxylation, regioselective epoxide ring opening, and vinyl __Grignard__ reactions are involved in generating the stereogenic centers C(4) and C(8), followed by __Grubbs‐II‐__catalyzed ring‐closing