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Catalytic asymmetric synthesis of the endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product from Ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S-TCPTTL)4.
J Org Chem. 2010 Sep 03; 75(17):6039-42.JO

Abstract

The reaction of a six-membered cyclic formyl-carbonyl ylide derived from alpha-diazo-beta-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh(2)(S-TCPTTL)(4), provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved.

Authors+Show Affiliations

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

20698712

Citation

Shimada, Naoyuki, et al. "Catalytic Asymmetric Synthesis of the Endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product From Ligusticum Chuanxing Via 1,3-dipolar Cycloaddition of a Formyl-derived Carbonyl Ylide Using Rh2(S-TCPTTL)4." The Journal of Organic Chemistry, vol. 75, no. 17, 2010, pp. 6039-42.
Shimada N, Hanari T, Kurosaki Y, et al. Catalytic asymmetric synthesis of the endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product from Ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S-TCPTTL)4. J Org Chem. 2010;75(17):6039-42.
Shimada, N., Hanari, T., Kurosaki, Y., Takeda, K., Anada, M., Nambu, H., Shiro, M., & Hashimoto, S. (2010). Catalytic asymmetric synthesis of the endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product from Ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S-TCPTTL)4. The Journal of Organic Chemistry, 75(17), 6039-42. https://doi.org/10.1021/jo101175b
Shimada N, et al. Catalytic Asymmetric Synthesis of the Endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product From Ligusticum Chuanxing Via 1,3-dipolar Cycloaddition of a Formyl-derived Carbonyl Ylide Using Rh2(S-TCPTTL)4. J Org Chem. 2010 Sep 3;75(17):6039-42. PubMed PMID: 20698712.
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TY - JOUR T1 - Catalytic asymmetric synthesis of the endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product from Ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S-TCPTTL)4. AU - Shimada,Naoyuki, AU - Hanari,Taiki, AU - Kurosaki,Yasunobu, AU - Takeda,Koji, AU - Anada,Masahiro, AU - Nambu,Hisanori, AU - Shiro,Motoo, AU - Hashimoto,Shunichi, PY - 2010/8/12/entrez PY - 2010/8/12/pubmed PY - 2010/12/14/medline SP - 6039 EP - 42 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 17 N2 - The reaction of a six-membered cyclic formyl-carbonyl ylide derived from alpha-diazo-beta-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh(2)(S-TCPTTL)(4), provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20698712/Catalytic_asymmetric_synthesis_of_the_endo_6_aryl_8_oxabicyclo[3_2_1]oct_3_en_2_one_natural_product_from_Ligusticum_chuanxing_via_13_dipolar_cycloaddition_of_a_formyl_derived_carbonyl_ylide_using_Rh2_S_TCPTTL_4_ L2 - https://doi.org/10.1021/jo101175b DB - PRIME DP - Unbound Medicine ER -