A Concise Asymmetric Synthesis of (–)-Virolin, (–)-Surinamensin, (–)-Raphidecursinol B and (–)-Polysphorin

Manda Nagaraju; Rajesh Chandra; Bhimrao B. Gawali

doi:10.1055/s-0031-1290678

Synlett, Table of Contents

Synlett 2012; 23(10): 1485-1488
DOI: 10.1055/s-0031-1290678

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A Concise Asymmetric Synthesis of (–)-Virolin, (–)-Surinamensin, (–)-Raphidecursinol B and (–)-Polysphorin

Manda Nagaraju

Organic Chemistry Division-II, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 706, India, Fax: +91(40)27193382 Email: gawalibb@yahoo.co.in

,

Rajesh Chandra

Organic Chemistry Division-II, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 706, India, Fax: +91(40)27193382 Email: gawalibb@yahoo.co.in

,

Bhimrao B. Gawali*

Organic Chemistry Division-II, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 706, India, Fax: +91(40)27193382 Email: gawalibb@yahoo.co.in

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Abstract

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Abstract

Highly concise and general asymmetric syntheses of biologically important natural (–)-8,4′-oxyneolignans [(–)-virolin, (–)-surinamensin, (–)-raphidecursinol B, and (–)-polysphorin] are reported. The key step in the synthesis is the Evan’s syn-aldol reaction to achieve the adducts with the desired stereochemistry. The four biologically important plant metabolites were synthesized using two common intermediates.

Key words

asymmetric synthesis - chiral auxiliary - aldol reaction - natural products - oxyneolignans

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References

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