Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum.
J Nat Prod. 2005 Sep; 68(9):1375-9.JN

Abstract

Arieianal (1) is a complex prenylated benzoic acid that was isolated from Piper arieianum. It has been synthesized through a convergent sequence that joins a functionalized diterpenoid chain to a protected aromatic core. Key steps include use of a copper enolate for selective displacement of an allylic bromide in the presence of an allylic acetate and a stereoselective Horner-Wadsworth-Emmons condensation to afford the desired E olefin of the isoprenoid side chain. After the diterpenoid chain was joined to the aromatic ring, use of sodium metal in hot sBuOH allowed selective cleavage of two benzyl ether protecting groups, and a sequence of oxidations gave the target compound. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to prepare more active analogues.

Authors+Show Affiliations

Odejinmi SI

Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA.

Wiemer DF

No affiliation info available

MeSH

BenzoatesMolecular StructureNuclear Magnetic Resonance, BiomolecularPiperStereoisomerism

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16180817

Citation

Odejinmi, Sina I., and David F. Wiemer. "Synthesis of Arieianal, a Prenylated Benzoic Acid From Piper Arieianum." Journal of Natural Products, vol. 68, no. 9, 2005, pp. 1375-9.

Odejinmi SI, Wiemer DF. Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum. J Nat Prod. 2005;68(9):1375-9.

Odejinmi, S. I., & Wiemer, D. F. (2005). Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum. Journal of Natural Products, 68(9), 1375-9.

Odejinmi SI, Wiemer DF. Synthesis of Arieianal, a Prenylated Benzoic Acid From Piper Arieianum. J Nat Prod. 2005;68(9):1375-9. PubMed PMID: 16180817.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum. AU - Odejinmi,Sina I, AU - Wiemer,David F, PY - 2005/9/27/pubmed PY - 2005/12/13/medline PY - 2005/9/27/entrez SP - 1375 EP - 9 JF - Journal of natural products JO - J Nat Prod VL - 68 IS - 9 N2 - Arieianal (1) is a complex prenylated benzoic acid that was isolated from Piper arieianum. It has been synthesized through a convergent sequence that joins a functionalized diterpenoid chain to a protected aromatic core. Key steps include use of a copper enolate for selective displacement of an allylic bromide in the presence of an allylic acetate and a stereoselective Horner-Wadsworth-Emmons condensation to afford the desired E olefin of the isoprenoid side chain. After the diterpenoid chain was joined to the aromatic ring, use of sodium metal in hot sBuOH allowed selective cleavage of two benzyl ether protecting groups, and a sequence of oxidations gave the target compound. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to prepare more active analogues. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/16180817/Synthesis_of_arieianal_a_prenylated_benzoic_acid_from_Piper_arieianum_ DB - PRIME DP - Unbound Medicine ER -

Tags

Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum.J Nat Prod. 2005 Sep; 68(9):1375-9.JN