Symmetry-assisted synthesis of triepoxide stereoisomers of E,Z,E,-dodeca-2,6,10-trien-1,12-diol and their cascade reactions to 2,5-linked bistetrahydrofurans

Abstract

Epoxidation des Triens (I) nach dem chiralen Sharpless‐Verfahren gibt ein Gemisch der d,l‐ [(IIa),(IIb)] und meso‐Isomeren (IIc) (‐ nicht meßbares ‐ Produktverhältnis theoretisch berechnet).

A Short and Efficient Enantiomeric Synthesis of Antitumor Fused Tetrahydrofurans

“…The reaction led to the expected mixture of two diastereomeric bis-epoxy alcohols. [12] In this process four stereocenters were introduced in a single step. Subsequent in situ protection of the primary hydroxy groups as tert-butyldimethylsilyl (TBS) ethers provided a diastereomeric mixture of bis-epoxides (R,R,R,R)-3 and (R,R,S,S)-3 in a 2.1:1 ratio, respectively.…”

Biomimetic Synthesis of Polyether Natural Products via Polyepoxide Opening

“…While working on the synthesis of uvaricin, the Hoye group reported studies on triepoxides 63-65 [152,153]. Their strategy involved release of the alcohol nucleophile via ester hydrolysis followed by a base-promoted Payne rearrangement (b) cascades cyclization of disubstituted 1,5,9-triepoxides reported by Hoye [152,153]; (c) support for the Payne rearrangement mechanism [154].…”

Recent Developments in the Synthesis of Annonaceous Acetogenins

“…nt-bullatacin (5) isopropylidene (D)-tartrate and ensuing Sharpless bisepoxidation." BF 3-promoted cyclization led to the symmetrical diol 7.2.…”