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Total synthesis of (+)-isatisine A.
Org Lett. 2011 Feb 04; 13(3):502-5.OL

Abstract

Total synthesis of (+)-isatisine A is described based on the application of a silyl-directed Mukaiyama-type [3 + 2]-annulation for the preparation of a fully substituted furan core. The indole branch forming the quaternary carbon center at C2 was constructed by addition to an intermediate N-acyliminium ion derived from aminal 4. In addition, the fused tetracyclic framework including furan core was built up using modified Buchwald amidation conditions.

Authors+Show Affiliations

Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

21188973

Citation

Lee, Jihoon, and James S. Panek. "Total Synthesis of (+)-isatisine A." Organic Letters, vol. 13, no. 3, 2011, pp. 502-5.
Lee J, Panek JS. Total synthesis of (+)-isatisine A. Org Lett. 2011;13(3):502-5.
Lee, J., & Panek, J. S. (2011). Total synthesis of (+)-isatisine A. Organic Letters, 13(3), 502-5. https://doi.org/10.1021/ol102848w
Lee J, Panek JS. Total Synthesis of (+)-isatisine A. Org Lett. 2011 Feb 4;13(3):502-5. PubMed PMID: 21188973.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (+)-isatisine A. AU - Lee,Jihoon, AU - Panek,James S, Y1 - 2010/12/28/ PY - 2010/12/30/entrez PY - 2010/12/30/pubmed PY - 2011/3/23/medline SP - 502 EP - 5 JF - Organic letters JO - Org Lett VL - 13 IS - 3 N2 - Total synthesis of (+)-isatisine A is described based on the application of a silyl-directed Mukaiyama-type [3 + 2]-annulation for the preparation of a fully substituted furan core. The indole branch forming the quaternary carbon center at C2 was constructed by addition to an intermediate N-acyliminium ion derived from aminal 4. In addition, the fused tetracyclic framework including furan core was built up using modified Buchwald amidation conditions. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21188973/Total_synthesis_of__+__isatisine_A_ L2 - https://doi.org/10.1021/ol102848w DB - PRIME DP - Unbound Medicine ER -