Saito, Sayuri; Yamakoshi, Hiroyuki; Nakamura, Seiichi published an article in 2019, the title of the article was Second-generation synthesis of a chiral building block for oxygenated terpenoids via a ring-contractive coupling with a secondary alcohol.Application In Synthesis of (2R,3S,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate And the article contains the following content:
A much improved second-generation synthesis of a chiral building block, developed for the syntheses of C17-oxygenated steroids/triterpenoids e.g., cortisol and C9-oxygenated labdane diterpenoids (marrubiin and marrulibacetal), was accomplished by exploiting a ring-contractive coupling between an α-bromo-δ-valerolactone (3R)/(3S)-I and (R)-seudenol, wherein the use of t-BuOK as a base allowed clean conversion to the corresponding tetrahydrofuran-2-carboxylate (2S)/(2R)-II even with a small excess of the alc. component. The experimental process involved the reaction of (2R,3S,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate(cas: 2873-29-2).Application In Synthesis of (2R,3S,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate
The Article related to terpenoid preparation, seudenol bromo valerolactone ring contraction coupling, Terpenes and Terpenoids: General and other aspects.Application In Synthesis of (2R,3S,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics