𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids–squalestatins by a cycloaddition–rearrangement strategy

✍ Scribed by David M. Hodgson; Carol Villalonga-Barber

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
126 KB
Volume
41
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Reaction of diazoketodiester 11 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate gives predominantly the 6,8-dioxabicyclo[3.2.1]octane 13. Acid-catalysed rearrangement of the corresponding alcohol 14 favours at equilibrium the 2,8-dioxabicyclo[3.2.1]octane skeleton 15 of the zaragozic acids±squalestatins.

📜 SIMILAR VOLUMES

A Symmetry-Based Synthesis of the Hetero
A Symmetry-Based Synthesis of the Heterobicyclic Core of the Zaragozic Acids/Squalestatins
✍ Yuzhou Wang; Olga Kataeva; Peter Metz 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 215 KB 👁 2 views

## Abstract The pseudo __C__~2~‐symmetrical diketone **22** was efficiently constructed from furan‐3,4‐dimethanol (**7**) using a two‐directional route featuring a double asymmetric dihydroxylation. Acidic hydrolysis of the cyclopentylidene acetals of **22** triggered a selective cyclization of the

Studies towards the synthesis of the zar
Studies towards the synthesis of the zaragozic acids: A novel epoxide cyclisation approach to the formation of the bicyclic acetal core
✍ Ian Paterson; Klaus Feßner; M.Raymond V Finlay; Mark F Jacobs 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 253 KB

Model studies towards the bicyclic acetal core 1 of the zaragozic acids, based on the epoxide cyclisation reaction 4 ---) 3, are described. Epoxide 14 provides the desired bicyclic acetal skeleton 16, while epoxide 27 leads through 28 to an isomeric acetal 30.

Total Synthesis of the Squalene Synthase
Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C by a Carbonyl Ylide Cycloaddition Strategy
✍ Seiichi Nakamura; Yuuki Hirata; Takahiro Kurosaki; Masahiro Anada; Osamu Kataoka 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 149 KB 👁 2 views

The zaragozic acids and squalestatins, a novel family of fungal metabolites isolated and characterized by researchers at Merck [1] and Glaxo, [2] respectively, in 1992, are the most potent inhibitors of squalene synthase known to date. [3] Some members of this family have also demonstrated the abili