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Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides.
Org Lett. 2010 Nov 19; 12(22):5226-9.OL

Abstract

The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

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Authors+Show Affiliations

Guéret SM
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
Furkert DP
No affiliation info available
Brimble MA
No affiliation info available

MeSH

CatalysisCrystallography, X-RayCyclizationMolecular ConformationMolecular StructureShellfish PoisoningSpiro CompoundsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

21028788

Citation

Guéret, Stéphanie M., et al. "Synthesis of a Functionalized 7,6-bicyclic Spiroimine Ring Fragment of the Spirolides." Organic Letters, vol. 12, no. 22, 2010, pp. 5226-9.
Guéret SM, Furkert DP, Brimble MA. Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides. Org Lett. 2010;12(22):5226-9.
Guéret, S. M., Furkert, D. P., & Brimble, M. A. (2010). Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides. Organic Letters, 12(22), 5226-9. https://doi.org/10.1021/ol102525w
Guéret SM, Furkert DP, Brimble MA. Synthesis of a Functionalized 7,6-bicyclic Spiroimine Ring Fragment of the Spirolides. Org Lett. 2010 Nov 19;12(22):5226-9. PubMed PMID: 21028788.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides. AU - Guéret,Stéphanie M, AU - Furkert,Daniel P, AU - Brimble,Margaret A, Y1 - 2010/10/28/ PY - 2010/10/30/entrez PY - 2010/10/30/pubmed PY - 2011/1/15/medline SP - 5226 EP - 9 JF - Organic letters JO - Org Lett VL - 12 IS - 22 N2 - The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21028788/Synthesis_of_a_functionalized_76_bicyclic_spiroimine_ring_fragment_of_the_spirolides_ L2 - https://doi.org/10.1021/ol102525w DB - PRIME DP - Unbound Medicine ER -