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Total synthesis of (+)-acanthodoral by the use of a Pd-catalyzed metal-ene reaction and a nonreductive 5-exo-acyl radical cyclization.
Org Lett. 2004 Feb 19; 6(4):537-40.OL

Abstract

[reaction: see text] The first total synthesis of the antibiotic acanthodoral (1) has been achieved from 3-methyl-2-cyclohexen-1-one in 19 steps in 2.1% overall yield. The synthesis features the use of a Pd-ene reaction in the presence of CO to form the endocyclic alkene 8, a nonreductive acyl radical cyclization reaction, and a ring contraction reaction by the Wolff rearrangement. (+)-Acanthodoral has also been synthesized starting from (+)-S-2,2-dimethyl-6-methylenecyclohexanecarboxylic acid.

Authors+Show Affiliations

Zhang L
Departments of Chemistry and Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Koreeda M
No affiliation info available

MeSH

AnimalsAnti-Bacterial AgentsCatalysisCyclizationCyclohexanecarboxylic AcidsIndicators and ReagentsMolecular StructureMolluscaNuclear Magnetic Resonance, BiomolecularPalladiumSesquiterpenesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

14961617

Citation

Zhang, Liming, and Masato Koreeda. "Total Synthesis of (+)-acanthodoral By the Use of a Pd-catalyzed Metal-ene Reaction and a Nonreductive 5-exo-acyl Radical Cyclization." Organic Letters, vol. 6, no. 4, 2004, pp. 537-40.
Zhang L, Koreeda M. Total synthesis of (+)-acanthodoral by the use of a Pd-catalyzed metal-ene reaction and a nonreductive 5-exo-acyl radical cyclization. Org Lett. 2004;6(4):537-40.
Zhang, L., & Koreeda, M. (2004). Total synthesis of (+)-acanthodoral by the use of a Pd-catalyzed metal-ene reaction and a nonreductive 5-exo-acyl radical cyclization. Organic Letters, 6(4), 537-40.
Zhang L, Koreeda M. Total Synthesis of (+)-acanthodoral By the Use of a Pd-catalyzed Metal-ene Reaction and a Nonreductive 5-exo-acyl Radical Cyclization. Org Lett. 2004 Feb 19;6(4):537-40. PubMed PMID: 14961617.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (+)-acanthodoral by the use of a Pd-catalyzed metal-ene reaction and a nonreductive 5-exo-acyl radical cyclization. AU - Zhang,Liming, AU - Koreeda,Masato, PY - 2004/2/14/pubmed PY - 2004/9/17/medline PY - 2004/2/14/entrez SP - 537 EP - 40 JF - Organic letters JO - Org Lett VL - 6 IS - 4 N2 - [reaction: see text] The first total synthesis of the antibiotic acanthodoral (1) has been achieved from 3-methyl-2-cyclohexen-1-one in 19 steps in 2.1% overall yield. The synthesis features the use of a Pd-ene reaction in the presence of CO to form the endocyclic alkene 8, a nonreductive acyl radical cyclization reaction, and a ring contraction reaction by the Wolff rearrangement. (+)-Acanthodoral has also been synthesized starting from (+)-S-2,2-dimethyl-6-methylenecyclohexanecarboxylic acid. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/14961617/Total_synthesis_of__+__acanthodoral_by_the_use_of_a_Pd_catalyzed_metal_ene_reaction_and_a_nonreductive_5_exo_acyl_radical_cyclization_ DB - PRIME DP - Unbound Medicine ER -