A convenient chiron approach to (4R,5R)-5-hydroxyalkylbutan-4-olides and the corresponding 7-oxa analogues from d-(+)-mannitol via an advanced common precursor: syntheses of (−)-muricatacin, 7-oxa-(−)-muricatacin, (4R,5R)-(−)-5-hydroxy-4-decanolide, and (4R,5R)-(−)-7-oxa-5-hydroxy-4-dodecanolide

A Decade of Muricatacin Synthesis and Beyond

“…In 2014, Bhaumik and co‐workers [ 25 ] developed a diversity oriented synthesis of (–)‐muricatacin ( 3 ), (–)‐ l ‐factor ( 8a ) and two of their oxa‐analogues from a common intermediate 57 obtained from d ‐(+)‐mannitol ( 54 ) (Scheme 9). Acetonide protection of d ‐mannitol ( 54 ) and selective terminal mono‐acetonide hydrolysis following literature procedure [ 46 ] gave 55 .…”

“…[ 13,14 ] Structure activity relationship (SAR) studies with several modifications of muricatacin structure are also documented. [ 15 ] Owing to its simple structure and promising biological activities, muricatacin has garnered much attention from the synthetic community and a plethora of synthetic strategies [ 14,16–34 ] have been developed for both enantiomers ( 3 and ent ‐ 3 ), their epimers ( 4a and 4b ), aza‐ and thia‐analogues ( 4c and 4d ), [ 16 ] the alkyl chain homologues ( 4e ), the alkyl chain oxa‐analogues ( 5a and 5b ), δ‐lactone and furofuranone analogues ( 6 and 7a–f ) (Figure 2) over the last nearly three decades. Many of these analogues show in vitro antitumor activity against several human cancer cell lines.…”

“…[ 17 ] Many aspects of muricatacin, its synthesis, bioactivity and that of analogues have been well doumented by Csáky in their report in 2010. [ 14 ] However, there has been many approaches [ 18–34 ] documented in the last decade (2010–2020) relying on different strategies with the chirality originating either through chiral pool, enantioselective catalysis, chiral resolutions or being induced by a chiral auxiliary (Scheme 1B). Acknowledging the broader landscape of this synthetic realm and that muricatacin or homologue serve as a start point for many higher acetogenins synthesis, [ 40 ] for e.g.…”