Preparation of the Three C1-C7, C8-C15, and C16-N22 Fragments of the Hsp90 Inhibitor Herbimycin A - Archive ouverte HAL Access content directly
Journal Articles SYNLETT Year : 2005

Preparation of the Three C1-C7, C8-C15, and C16-N22 Fragments of the Hsp90 Inhibitor Herbimycin A

Abstract

The construction of the three C16-N22 2, C1-C7 6 (as 23) and C8-C15 5 (as 32) segments of the Hsp90 inhibitor herbimycin A (1) is reported. 1-Iodo-3-nitro-2,5-diphenol compound 2 was obtained in 55% yield for 3 steps from the commercially available diiodo derivative 7. Reaction between 1,1-dibromo-alkene 22 and vinyltin 17a using Pd(PPh3)4 or Pd(CH3CN)2Cl2/CuI/diisopropylethylamine, in toluene or DMF at 85 °C, led to enyne 23 in 63% yield (19% overall yield from isopropylidene glyceraldehyde). The synthesis of the C8-C15 sub-unit 32 was performed in 3.4% overall yield for 13 steps, from the commercially available ester 24, with a Hoppe crotylation as a key step.
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Dates and versions

hal-03333714 , version 1 (03-09-2021)

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Sylvie Centonze-Audureau, François-Hugues Porée, Jean-François Betzer, Jean-Daniel Brion, Ange Pancrazi, et al.. Preparation of the Three C1-C7, C8-C15, and C16-N22 Fragments of the Hsp90 Inhibitor Herbimycin A. SYNLETT, 2005, 2005 (06), pp.0981-0985. ⟨10.1055/s-2005-864804⟩. ⟨hal-03333714⟩
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