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Asymmetric epoxide cyclisation route to the F-pyran fragment of the altohyrtins and key aldol studies

Anderson, JC; McDermott, BP; Griffin, EJ; (2000) Asymmetric epoxide cyclisation route to the F-pyran fragment of the altohyrtins and key aldol studies. TETRAHEDRON , 56 (44) 8747 - 8767.

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Abstract

The evolution of an asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins is described, which relies on a key intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. The C-38-C-39 epoxide stereochemistry was achieved through optimisation of substrate control. Key aldol studies towards coupling the F-pyran ring with an E-pyran ring precursor was investigated, but unsuccessful. (C) 2000 Elsevier Science Ltd. All rights reserved.

Type:Article
Title:Asymmetric epoxide cyclisation route to the F-pyran fragment of the altohyrtins and key aldol studies
Keywords:asymmetric synthesis, epoxidation, aldol reactions, pyran, SPONGE HYRTIOS-ALTUM, POTENT CYTOTOXIC MACROLIDES, MARINE SPONGE, ENANTIOSELECTIVE SYNTHESIS, C SPONGISTATIN-2, STEREOSELECTIVE CONSTRUCTION, ABSOLUTE STEREOSTRUCTURES, CONVERGENT APPROACH, ALLYLIC ALCOHOLS, SUBUNIT
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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