First Generation Retrosynthetic Analysis of FR901464

March 01, 2024

• Title:       

  First Generation Retrosynthetic Analysis of FR901464

• Image Source:

  Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue

• Mark:

  Scheme 1

• Associated context:

  Scheme 1 shows our first generation retrosynthetic analysis of FR901464. We envisioned a Nozaki-Hiyama-Kishi (NHK) reaction of 1 and 2 as the final coupling reaction because the reaction conditions are mild and it is generally in accordance with Felkin selectivity for additions to R-chiral aldehydes. Vinyl iodide 1 would be prepared from acid 3 and amine 4 that were expected  to be derived from propargylic alcohol 6 and the L-threonine  derivative 7, respectively. Ketoaldehyde 2 could be prepared  from allylic alcohol 5 by oxidative cleavages of both olefins. Finally, this alcohol would arise from epoxyalcohol 8.