Synthesis of Immucillins BCX‐1777and BCX‐4430 from a Common Precursor

A convergent route for the synthesis of BCX‐1777 and BCX‐4430 from a Boc‐protected 2‐pyrrolidinone, derived from 2,3,5‐tri‐O‐benzyl‐d‐ribonolactone, and a dihalogenated pyrrolopyrimidine as the key starting materials is reported. A chemoselective cross‐coupling was achieved from the two key starting...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-07, Vol.2022 (25)
Main Authors: Krishnakumar, K A, Lankalapalli, Ravi S
Format: Article
Language:English
Subjects:
Cross coupling
Precursors
Stereoselectivity
Synthesis
Online Access:Get full text
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Summary:A convergent route for the synthesis of BCX‐1777 and BCX‐4430 from a Boc‐protected 2‐pyrrolidinone, derived from 2,3,5‐tri‐O‐benzyl‐d‐ribonolactone, and a dihalogenated pyrrolopyrimidine as the key starting materials is reported. A chemoselective cross‐coupling was achieved from the two key starting materials in 79 % yield. Luche reduction and mesylation resulted in the stereoselective formation of an advanced intermediate in 77 % yield over two steps, which served as a precursor for synthesizing BCX‐1777 and BCX‐4430 in 38 % (over 10 steps) and 32 % (over 11 steps) overall yields, respectively, from 2,3,5‐tri‐O‐benzyl‐d‐ribonolactone.Dedicated to the students in my lab for their perseverance during the COVID-19 pandemic
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200428