11 Questions
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?
They are naturally occurring biologically active compounds and are toxic against brine shrimp larvae.
What was the occasion for which the issue was dedicated to Professor S.V. Kessar?
His 70th birthday
What are the key methods involved in the preparation of aromatic A ring 9,10-secosteroids?
pyrolysis, radical initiated processes, and microbial transformations
What severe limitations do the procedures involving the preparation of aromatic A ring 9,10-secosteroids have?
severe limitations towards the manipulation and interconversion of substituents required in a natural product
What is the key step in the convergent synthesis of Calicoferol E?
radical coupling of des-AB-cholest-8methyledine-9-one with 2-methyl-4MEM ether of benzyl iodide
What is the overall yield of the reported 14 step synthesis of Calicoferol E?
6.6%
What are the techniques used in the synthesis of Calicoferol E using 9αhydroxycholesta-1,4-diene-3-one?
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
What are the major products obtained from the deketalization of 9α-hydroxy-3-ethylenedioxy cholestane 4?
9αhydroxycholestane-1,4-diene-3-one (5) and Calicoferol E (6)
Test your knowledge on the synthesis of Calicoferol E with this chemistry research quiz. The quiz is based on the research paper 'Issue in Honor of Prof. S. V. Kessar ARKIVOC 2002 (vii) 82-90' by Tej Vir Singh, Raminder Kaur, Keshav Rai Agnihotri, and Manoj Bali.
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