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Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids.
Org Lett. 2006 Oct 12; 8(21):4959-61.OL

Abstract

[reaction: see text] Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.

Authors+Show Affiliations

Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia. mgb@rcs.anu.edu.auNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17020346

Citation

Banwell, Martin G., et al. "Concise Assembly of the Polycyclic Frameworks Associated With the Hapalindole and Fischerindole Alkaloids." Organic Letters, vol. 8, no. 21, 2006, pp. 4959-61.
Banwell MG, Ma X, Taylor RM, et al. Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids. Org Lett. 2006;8(21):4959-61.
Banwell, M. G., Ma, X., Taylor, R. M., & Willis, A. C. (2006). Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids. Organic Letters, 8(21), 4959-61.
Banwell MG, et al. Concise Assembly of the Polycyclic Frameworks Associated With the Hapalindole and Fischerindole Alkaloids. Org Lett. 2006 Oct 12;8(21):4959-61. PubMed PMID: 17020346.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids. AU - Banwell,Martin G, AU - Ma,Xinghua, AU - Taylor,Rebecca M, AU - Willis,Anthony C, PY - 2006/10/6/pubmed PY - 2007/6/28/medline PY - 2006/10/6/entrez SP - 4959 EP - 61 JF - Organic letters JO - Org Lett VL - 8 IS - 21 N2 - [reaction: see text] Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17020346/Concise_assembly_of_the_polycyclic_frameworks_associated_with_the_hapalindole_and_fischerindole_alkaloids_ L2 - https://doi.org/10.1021/ol062020x DB - PRIME DP - Unbound Medicine ER -