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

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-sp...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (38), p.9072-9079
Main Authors: Kunkalkar, Rupesh A, Laha, Debasish, Fernandes, Rodney A
Format: Article
Language:English
Subjects:
Acetogenins - chemical synthesis
Acetogenins - chemistry
Alkylation
Catalysis
Chemistry Techniques, Synthetic
Furans - chemical synthesis
Furans - chemistry
Stereoisomerism
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Summary: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-sp 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01721e