title: De novo protecting-group-free total synthesis of (+)-muricadienin, (+)-ancepsenolide and (+)-3-hexadecyl-5-methylfuran-2(5H)-one.
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-sp3Sonogashira 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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in.
authors.forename: Rupesh A
authors.initials: RA
authors.lastname: Kunkalkar
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in.
authors.forename: Debasish
authors.initials: D
authors.lastname: Laha
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in.
authors.forename: Rodney A
authors.initials: RA
authors.lastname: Fernandes
mesh_terms: D054378:Acetogenins / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000626224:3-hexadecyl-5-methylfuran-2(5H)-one; D054378:Acetogenins; D005663:Furans; C000626225:ancepsenolide; C000599601:muricadienin