First Stereoselective Total Synthesis of Cryptomoscatone D2 and Syntheses of (5R,7S)-Kurzilactone and (+)-Cryptofolione by an Asymmetric Acetate Aldol Approach

Jhillu Singh Yadav; Bogonda Ganganna; Dinesh Chandra Bhunia

doi:10.1055/s-0031-1290771

Synthesis, Table of Contents

Synthesis 2012; 44(9): 1365-1372
DOI: 10.1055/s-0031-1290771

paper

First Stereoselective Total Synthesis of Cryptomoscatone D2 and Syntheses of (5R,7S)-Kurzilactone and (+)-Cryptofolione by an Asymmetric Acetate Aldol Approach

Jhillu Singh Yadav*

Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in

,

Bogonda Ganganna

Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in

,

Dinesh Chandra Bhunia

Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in

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Abstract

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Abstract

An efficient concise stereoselective total synthesis of cryptomoscatone D2 and syntheses of (5R,7S)-kurzilactone and (+)-cryptofolione, based on an asymmetric acetate aldol reaction starting from trans-cinnamaldehyde, are described. The other key reactions are a Horner–Wadsworth–Emmons reaction, a Brown’s asymmetric allylation and a ring-closing metathesis.

Key words

lactones - stereoselective synthesis - total synthesis - aldol reactions - cyclizations

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References

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