The Potential of β‐Hydroxy‐γ‐vinyl‐γ‐lactone in the Synthesis of Natural Products and Beyond

Abstract

In this mini‐review, we have abstracted the syntheses of β‐hydroxy‐γ‐vinyl‐γ‐lactone and the different tactics and strategies adopted using this important building block in the synthesis of various natural products. Apart from this, the lactone in having a strategic vinyl bond was contemplated as allyl donor in Pd‐catalyzed allylic arylation and also in a cascade Prins‐Ritter reaction. This building block was visualized to be a desymmetrized 3,4‐dihydroxy‐hexyl unit providing orthogonal functional groups for various useful transformations. The active α‐position is available for alkylation, the γ‐vinyl bond, the lactone carbonyl and the β‐hydroxy groups add value to this building block for various possible conversions to natural products and beyond.

Advances in Total Synthesis of Some 2,3,5‐Trisubstituted Tetrahydrofuran Natural Products

“…We completed one of the shortest protecting-groupfree synthesis of Hagen's gland lactones from D-glucono-δlactone in 2012 (Scheme 37) and further improved it by catalytic hydro-deiodination. [14] The synthesis began from D-glucono-δlactone 242, which was converted in a one-pot procedure into β-hydroxy-γ-vinyl-γ-lactone 243 [98] (Scheme 37). Next, the cross metathesis with either 244 a or 244 b led to the lactones 245 a (94%) and 245 b (81%), respectively.…”

A Decade of Muricatacin Synthesis and Beyond

“…[ 26 ] Following our group one‐pot procedure, the lactone 59 was converted into the useful building block β‐hydroxy‐γ‐vinyl‐γ‐lactone 60 . [ 47 ] Next, the lactone reduction and acetonide formation to 61 and cross‐metathesis with ethyl acrylate gave alcohol 62 . Further, oxidation to aldehyde and Wittig olefination resulted in 63 that on olefin reduction and lactonization furnished (–)‐muricatacin ( 3 ).…”

Novel Au(I)-Based Artificial Metallo-Cycloisomerase for Catalyzing the Cycloisomerization of γ-Alkynoic Acids

“…Vinyl lactones are the basic units of many natural products and are of high synthetic value. 16,17 In the last decades, the reaction has become a benchmark reaction. 18 Ferritin is a self-assembled protein cage that is composed of 24 subunits (Figure 1A), and it has a diameter of 12 and an 8 nm cavity (Figure 1B).…”

“…The cycloisomerization reaction of γ-alkynoic acid is one of the most convenient methods for the preparation of vinyl lactones, which has a desirable atomic and stepwise economy. Vinyl lactones are the basic units of many natural products and are of high synthetic value. , In the last decades, the reaction has become a benchmark reaction …”