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Total Synthesis of Pradimicinone, the Common Aglycon of the Pradimicin–Benanomicin Antibiotics

✍ Scribed by Mitsuru Kitamura; Ken Ohmori; Toshihisa Kawase; Keisuke Suzuki

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
111 KB
Volume
38
Category
Article
ISSN
0044-8249

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✦ Synopsis

A benzo[a]naphthacenequinone core, an amino acid, and a disaccharide are the constituents of pradimicin-benanomicin antibiotics 1 (R =disaccharide), a class of natural products with significant antifungal and anti-HIV activities. The first total synthesis of pradimicinone (benanomicinone, 1; R =H), the common aglycon of this class of natural products, has now been achieved based on the transmission of chirality during the pinacol cyclization of 2,2'-biaryldicarbaldehydes.

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✍ Ian Paterson; Robert D. M. Davies; Rodolfo Marquez 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 109 KB 👁 1 views

The callipeltosides were isolated by Minale and co-workers from the shallow-water lithistid sponge Callipelta sp., collected off the east coast of New Caledonia. [1a,b] Callipeltoside A (1 in Scheme 1, obtained in 1.4 Â 10 À4 % yield) was found to inhibit in vitro the proliferation of KB and P388 ce