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Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene.
Org Lett. 2009 Mar 19; 11(6):1441-3.OL

Abstract

The enantioselective total syntheses of enokipodins A and B, alpha-cuparenone-type sesquiterpenoids with antimicrobial activity, have been achieved. The key step is the enantiospecific construction of the quaternary carbon center using a palladium-catalyzed addition of an arylboronic acid to an allene followed by an Eschenmoser-Claisen rearrangement.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yoshida M
Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima, 770-8505, Japan. yoshida@ph.tokushima-u.ac.jp
Shoji Y
No affiliation info available
Shishido K
No affiliation info available

MeSH

AlkadienesAnti-Bacterial AgentsAntifungal AgentsBiological ProductsBoronic AcidsCatalysisCyclizationMolecular StructurePalladiumSesquiterpenesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19245241

Citation

Yoshida, Masahiro, et al. "Total Syntheses of Enokipodins a and B Utilizing Palladium-catalyzed Addition of an Arylboronic Acid to an Allene." Organic Letters, vol. 11, no. 6, 2009, pp. 1441-3.
Yoshida M, Shoji Y, Shishido K. Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene. Org Lett. 2009;11(6):1441-3.
Yoshida, M., Shoji, Y., & Shishido, K. (2009). Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene. Organic Letters, 11(6), 1441-3. https://doi.org/10.1021/ol9001637
Yoshida M, Shoji Y, Shishido K. Total Syntheses of Enokipodins a and B Utilizing Palladium-catalyzed Addition of an Arylboronic Acid to an Allene. Org Lett. 2009 Mar 19;11(6):1441-3. PubMed PMID: 19245241.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene. AU - Yoshida,Masahiro, AU - Shoji,Yasunobu, AU - Shishido,Kozo, PY - 2009/2/28/entrez PY - 2009/2/28/pubmed PY - 2009/4/10/medline SP - 1441 EP - 3 JF - Organic letters JO - Org Lett VL - 11 IS - 6 N2 - The enantioselective total syntheses of enokipodins A and B, alpha-cuparenone-type sesquiterpenoids with antimicrobial activity, have been achieved. The key step is the enantiospecific construction of the quaternary carbon center using a palladium-catalyzed addition of an arylboronic acid to an allene followed by an Eschenmoser-Claisen rearrangement. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19245241/Total_syntheses_of_enokipodins_A_and_B_utilizing_palladium_catalyzed_addition_of_an_arylboronic_acid_to_an_allene_ L2 - https://doi.org/10.1021/ol9001637 DB - PRIME DP - Unbound Medicine ER -