Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP₁ (I) and deoxypreussomerin A (II) in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone.Polymer-bound triphenylphosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs.Preliminary biol. evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors.

01 Sep 2000·European Journal of Organic Chemistry

Secondary metabolites by chemical screening. 42 Cladospirones B to I from Sphaeropsidales sp. F-24'707 by variation of culture conditions

Author: Helge Björn Bode ; Martina Walker ; Axel Zeeck

Variation of the culture conditions - static surface cultures in particular - of the fungus Sphaeropsidales sp. (strain F-24'707), which produces cladospirone bisepoxide, led to the isolation of eight new spirobisnaphthalenes - the cladospirones B → I - together with seven known representatives of this class of secondary metabolites.Cladospirones C (I) and D (II) show antibiotic activity against bacteria and algae.The structures of cladospirone B (III) and E (IV) were confirmed by X-ray structure anal.I and cladospirones G → I represent new members of the spirobisnaphthalene family, thanks to their hydroxylation patterns.Moreover, they underline the extraordinary status of this interesting class of compounds as the most diverse secondary metabolites, allowing for their small number of carbon atoms, described to date.Almost all possible permutations of stereochem. and oxygen substitution pattern on the C₁₀ skeleton are produced by different fungi.

01 Jan 1999·Journal of the Chemical Society, Perkin Transactions 1

The synthesis of 1,8-dihydroxynaphthalene-derived natural products: palmarumycin CP1, palmarumycin CP2, palmarumycin C11, CJ-12,371, deoxypreussomerin A and novel analogues

Author: Alcaraz, Marie-Lyne ; Steeneck, Christoph ; Taylor, Richard J. K. ; Ragot, Jacques P.

Total syntheses of the title fungal metabolites, I, II, III, IV and V, resp., are described via a route which utilizes initial acetalization with 1,8-dihydroxynaphthalene followed by elaboration of the ring A functionality.Novel analogs are also reported.Structural clarification is provided for palmarumycin C₁₁ (III), bipendensin and Sch 53,823.

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Neoplasms	Preclinical	-	Merck Sharp & Dohme Corp.	-

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