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A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products

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JournalOrganic and Biomolecular Chemistry
DatePublished - 7 Jan 2003
Issue number1
Volume1
Number of pages13
Pages (from-to)104-116
Original languageEnglish

Abstract

A synthesis of apicularen precursor (-)-6 in 18 steps from D-glucal is reported. As (+)-6 has been converted into the potent, naturally occurring salicylate anti-cancer agent, (-)-apicularen A in 8 steps, this study constitutes a formal total synthesis of (+)-apicularen A. Key steps in the synthetic route include: (i) Useful D-glucal elaboration processes, (ii) organometallic displacements at carbohydrate C-6 triflates using Knochel-type and related functionalised, aromatic Grignard reagents, (iii) stereoselective allyltrimethylsilane-acetal reactions generating C-allyl systems, (iv) stereocontrolled aldehyde allylation processes from both substrate and reagent, and (v) a novel Keck-type macrolactonisation. In addition, preliminary studies are reported in which a procedure has been devised to convert apicularen-derived intermediates into salicylihalamide-like products.

    Research areas

  • CHONDROMYCES SPECIES MYXOBACTERIA, ENANTIOSELECTIVE TOTAL SYNTHESIS, RING-CLOSING-METATHESIS, NATURAL-PRODUCTS, CYTOTOXIC MACROLIDES, MAGNESIUM EXCHANGE, COUPLING REACTIONS, GRIGNARD-REAGENTS, CORE STRUCTURE, OXIMIDINE-II

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