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Issue 38, 2016
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De novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one

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Abstract

A de novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one has been achieved. Ring-closing-metathesis has been the key step in the synthesis. In (+)-muricadienin synthesis, a long chain alkyl group has been installed by an sp–sp3 Sonogashira type reaction followed by a cis-selective Lindlar reduction. The total synthesis is achieved in 7 steps and in excellent 43.5% overall yield. Similarly, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one synthesis is completed in 5 steps each and in 48 and 68% overall yields, respectively.

Graphical abstract: De novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one

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Supplementary files

Article information


Submitted
09 Aug 2016
Accepted
30 Aug 2016
First published
30 Aug 2016

Org. Biomol. Chem., 2016,14, 9072-9079
Article type
Paper

De novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one

R. A. Kunkalkar, D. Laha and R. A. Fernandes, Org. Biomol. Chem., 2016, 14, 9072
DOI: 10.1039/C6OB01721E

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