Synthesis of Calicoferol E - Chemistry Research Quiz

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Questions and Answers

What is the key feature of the synthesis of Calicoferol E?

The acid catalyzed rearrangement of 9α-hydroxycholest-1,4-diene-3one to give Calicoferol E

What are the key compounds used in the synthesis?

5α-cholestan-3β-ol and DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone)

Where was the synthesis work conducted?

Department of Chemistry, Panjab University, Chandigarh, India

What is the significance of 9,10-secosteroids like Calicoferol E and Astrogorgiadiol?

<p>They are naturally occurring biologically active compounds and are toxic against brine shrimp larvae.</p> Signup and view all the answers

What was the occasion for which the issue was dedicated to Professor S.V. Kessar?

<p>His 70th birthday</p> Signup and view all the answers

What are the key methods involved in the preparation of aromatic A ring 9,10-secosteroids?

<p>pyrolysis, radical initiated processes, and microbial transformations</p> Signup and view all the answers

What severe limitations do the procedures involving the preparation of aromatic A ring 9,10-secosteroids have?

<p>severe limitations towards the manipulation and interconversion of substituents required in a natural product</p> Signup and view all the answers

What is the key step in the convergent synthesis of Calicoferol E?

<p>radical coupling of des-AB-cholest-8methyledine-9-one with 2-methyl-4MEM ether of benzyl iodide</p> Signup and view all the answers

What is the overall yield of the reported 14 step synthesis of Calicoferol E?

<p>6.6%</p> Signup and view all the answers

What are the techniques used in the synthesis of Calicoferol E using 9αhydroxycholesta-1,4-diene-3-one?

<p>deprotection of a 1,3-dioxalane derivative to ketone, dehydrogenation of 9α-hydroxy-5α-cholestan-3-one, and the chemistry of acid catalyzed dienone-phenol rearrangement</p> Signup and view all the answers

What are the major products obtained from the deketalization of 9α-hydroxy-3-ethylenedioxy cholestane 4?

<p>9αhydroxycholestane-1,4-diene-3-one (5) and Calicoferol E (6)</p> Signup and view all the answers

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