853211-61-7

Upstream product

• 853211-36-6 (E)-(3S,4R,7S)-3,7-Dimethyl-8-(tetrahydro-pyran-2-yloxy)-oct-5-en-1-yn-4-ol 
• 65-85-0 benzoic acid 
• 110-87-2 3,4-dihydro-2H-pyran 
• 88588-59-4 (2S)-2-methyl-3-(tetrahydropyran-2-yloxy)propan-1-ol 
• 88557-53-3 (R)-2-Methyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester 
• 853211-57-1 (E)-(S)-4-Methyl-5-(tetrahydro-pyran-2-yloxy)-pent-2-en-1-ol 
• 853211-32-2 (E)-(S)-4-Methyl-5-(tetrahydro-pyran-2-yloxy)-pent-2-enal 
• 206998-23-4 (E)-(S)-4-Methyl-5-(tetrahydro-pyran-2-yloxy)-pent-2-enoic acid methyl ester 
• 73992-01-5 (2S)-2-methyl-3-(tetrahydro-2H-pyran-2-oxy)propanal 
• 853211-34-4 Diisopropyl-carbamic acid (1Z,5E)-(3S,4R,7S)-4-hydroxy-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl ester 

Relevant academic research and scientific papers

Preparation of the three C1-C7, C8-C15, and C16-N22 fragments of the Hsp90 inhibitor herbimycin A

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. l-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.