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Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach.
J Org Chem. 2012 Aug 17; 77(16):6989-97.JO

Abstract

The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Pasqua AE
School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
Ferrari FD
No affiliation info available
Hamman C
No affiliation info available
Liu Y
No affiliation info available
Crawford JJ
No affiliation info available
Marquez R
No affiliation info available

MeSH

AlkenesAmidesAntifungal AgentsBoron CompoundsMagnetic Resonance SpectroscopyMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22804781

Citation

Pasqua, Adele E., et al. "Step-economic Synthesis of (+)-crocacin C: a Concise Crotylboronation/[3,3]-sigmatropic Rearrangement Approach." The Journal of Organic Chemistry, vol. 77, no. 16, 2012, pp. 6989-97.
Pasqua AE, Ferrari FD, Hamman C, et al. Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach. J Org Chem. 2012;77(16):6989-97.
Pasqua, A. E., Ferrari, F. D., Hamman, C., Liu, Y., Crawford, J. J., & Marquez, R. (2012). Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach. The Journal of Organic Chemistry, 77(16), 6989-97. https://doi.org/10.1021/jo301210f
Pasqua AE, et al. Step-economic Synthesis of (+)-crocacin C: a Concise Crotylboronation/[3,3]-sigmatropic Rearrangement Approach. J Org Chem. 2012 Aug 17;77(16):6989-97. PubMed PMID: 22804781.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Step-economic synthesis of (+)-crocacin C: a concise crotylboronation/[3,3]-sigmatropic rearrangement approach. AU - Pasqua,Adele E, AU - Ferrari,Frank D, AU - Hamman,Chris, AU - Liu,Yanzhou, AU - Crawford,James J, AU - Marquez,Rodolfo, Y1 - 2012/08/02/ PY - 2012/7/19/entrez PY - 2012/7/19/pubmed PY - 2012/12/20/medline SP - 6989 EP - 97 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 16 N2 - The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22804781/Step_economic_synthesis_of__+__crocacin_C:_a_concise_crotylboronation/[33]_sigmatropic_rearrangement_approach_ L2 - https://doi.org/10.1021/jo301210f DB - PRIME DP - Unbound Medicine ER -