A new route to tricyclane sesquiterpenoids: total synthesis of α-ekasantalic acid

Abstract

Chemical manipulation of the cycloadduct of citraconic anhydride and cyclopentadiene enables a new synthetic route to tricyclane sesquiterpenoids.

A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation

“…Consequently, the synthesis of bridged [2,2,1] bicyclic lactones received wide attentions and several approaches have been developed. The typical methods include Baeyer–Villiger oxidation 6 , esterification 7 , 8 , halolactonization 9 , 10 , electrocatalytic reaction 11 , and others 12 – 14 . However, most of these approaches focused on the synthesis of racemic bridged [2,2,1] bicyclic lactones and multistep synthesis was necessary to achieve these transformations.…”

Efforts toward the Total Synthesis of Elisabethin A

“…Unfortunately, all attempts to reduce esters ( Z )-22 and ( E )-22 into the desired C-7 methyl ester 8 were unsuccessful. − Inspired by our second approach (see below), in our next attempt to create a C-7 chiral center, we planned to perform conjugated addition of methyl cuprate to lactone 27 (Scheme ), a reaction that was successful for a similar substrate.…”

Total Synthesis of Terpenes and Their Biological Significance: A Critical Review

“…TBS ether (91) was used to protect the hydroxymethyl carbon of ester (90). Lithium borohydride has been used to reduce γ-lactone (91), yielding diol (92). IBX has been used to cleanly oxidize diol (92), yielding aldehyde (93).…”

“…Lithium borohydride has been used to reduce γ-lactone (91), yielding diol (92). IBX has been used to cleanly oxidize diol (92), yielding aldehyde (93).…”