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Total Synthesis of Aculeatins A and B from L-Malic Acid

✍ Scribed by Jhillu S. Yadav; Yerragorla Gopala Rao; Dandekar Chandrakanth; Kontham Ravindar; Basi V. Subba Reddy

Book ID
102256567
Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
160 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

An efficient total synthesis of the cytotoxic spiroketal natural products aculeatin A and B is described. The synthesis of the 1,3,5-triol moiety with appropriate configuration was accomplished from the commercially available l-malic acid. The key steps in this synthesis are the Barbier allylation, LiAlH 4 /LiI-mediated syn-stereoselective 1,3-asymmetric reduction, and phenyliodine bis(trifluoroacetate) (ΒΌ [bis(trifluoroacetoxy)iodo]benzene; PIFA) mediated oxidative spirocyclization. Scheme 1. Retrosynthetic Analysis of Aculeatin A (1) and Aculeatin B (2)

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✍ Eva Falomir; Paula Alvarez-Bercedo; Miguel Carda; J. Alberto Marco πŸ“‚ Article πŸ“… 2006 πŸ› John Wiley and Sons βš– 12 KB πŸ‘ 2 views

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