Abstract:Pimarane diterpenes are produced by a diverse array of
plants,
fungi, and bacteria. Many members of this family possess antimicrobial
and antiproliferative activities. The pimarane diterpenes are characterized
by a tricyclic carbon scaffold comprising three fused six-membered
rings and at least three quaternary centers. Here, we describe two
convergent, fragment-based strategies toward the synthesis of diaporthein
B (3), one of the most highly oxidized pimarane diterpenes.
The first approach provided access to… Show more
“…The α-alkylation of aldehydes and ketones is among the most crucial carbon–carbon bond-forming reactions in organic chemistry and indispensable for synthesizing numerous biologically active compounds and natural products. − In many cases, stereocontrol is needed to force the formation of one defined product. Significant efforts have been made to develop enantioselective methods, primarily relying on chiral auxiliaries .…”
“…The α-alkylation of aldehydes and ketones is among the most crucial carbon–carbon bond-forming reactions in organic chemistry and indispensable for synthesizing numerous biologically active compounds and natural products. − In many cases, stereocontrol is needed to force the formation of one defined product. Significant efforts have been made to develop enantioselective methods, primarily relying on chiral auxiliaries .…”
Aromatic ent-pimaranes are a group of aromatized tricyclic diterpenoids which exhibit diverse bioactivities. In this work, the first total syntheses of two aromatic ent-pimaranes were achieved via a C-ABC construction...
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