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Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of bromoallenes.
Org Lett. 2009 Oct 01; 11(19):4478-81.OL

Abstract

Palladium(0)-catalyzed cyclization of bromoallenes bearing hydroxyl and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. With this bis-cyclization as the key step, a short total synthesis of pachastrissamine, a biologically active marine natural product, was achieved.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Inuki S
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Yoshimitsu Y
No affiliation info available
Oishi S
No affiliation info available
Fujii N
No affiliation info available
Ohno H
No affiliation info available

MeSH

AlkadienesCatalysisCyclizationMolecular StructurePalladiumSphingosineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19739618

Citation

Inuki, Shinsuke, et al. "Ring-construction/stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (jaspine B) Through Palladium-catalyzed Bis-cyclization of Bromoallenes." Organic Letters, vol. 11, no. 19, 2009, pp. 4478-81.
Inuki S, Yoshimitsu Y, Oishi S, et al. Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of bromoallenes. Org Lett. 2009;11(19):4478-81.
Inuki, S., Yoshimitsu, Y., Oishi, S., Fujii, N., & Ohno, H. (2009). Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of bromoallenes. Organic Letters, 11(19), 4478-81. https://doi.org/10.1021/ol901904w
Inuki S, et al. Ring-construction/stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (jaspine B) Through Palladium-catalyzed Bis-cyclization of Bromoallenes. Org Lett. 2009 Oct 1;11(19):4478-81. PubMed PMID: 19739618.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of bromoallenes. AU - Inuki,Shinsuke, AU - Yoshimitsu,Yuji, AU - Oishi,Shinya, AU - Fujii,Nobutaka, AU - Ohno,Hiroaki, PY - 2009/9/11/entrez PY - 2009/9/11/pubmed PY - 2009/12/16/medline SP - 4478 EP - 81 JF - Organic letters JO - Org Lett VL - 11 IS - 19 N2 - Palladium(0)-catalyzed cyclization of bromoallenes bearing hydroxyl and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. With this bis-cyclization as the key step, a short total synthesis of pachastrissamine, a biologically active marine natural product, was achieved. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19739618/Ring_construction/stereoselective_functionalization_cascade:_total_synthesis_of_pachastrissamine__jaspine_B__through_palladium_catalyzed_bis_cyclization_of_bromoallenes_ L2 - https://doi.org/10.1021/ol901904w DB - PRIME DP - Unbound Medicine ER -