The total synthesis of the archaebacterial C40-diol and its enantiomer based on (R)-5-acetoxy-4-methylpentanoic acid

A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide

“… [4] This C 40 ‐unit was later also synthesized by Czeskis. [5] Still much is unknown about the biosynthesis of these macrocyclic archaeal lipids. It is unclear how the macrocycle is formed, which enzymes are involved in this process or even the exact structures of the precursors.…”

“…The stereochemistry of the methyl substituents was established by the Heathcock group, who synthesized the C 40 ‐lipid chain [4] . This C 40 ‐unit was later also synthesized by Czeskis [5] . Still much is unknown about the biosynthesis of these macrocyclic archaeal lipids.…”

Straightforward Synthesis of Chiral Terpenoid Building Blocks by Ru-Catalyzed Enantioselective Hydrogenation

“…Easily available geraniol was also submitted to enzymatic double hydrogenation in the presence of Saccharomyces cerevisiae with excellent stereoselectivities but with a low yield . Chiral pools such as methyl ( R )-3-hydroxy-2-methylpropionate, ( R )-citronellol, , (−)-isopulegol, and (4 R )-5-acetoxy-4-methylpentanoic acid have been investigated for the synthesis of the 2,6-dimethyloctane chiron.…”

A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide

“…[4] This C 40 -unit was later also synthesized by Czeskis. [5] Still much is unknown about the biosynthesis of these macrocyclic archaeal lipids.It is unclear how the macrocycle is formed, which enzymes are involved in this process or even the exact structures of the precursors. [6] Evolutionary unrelated, syn-1,5 methyl-branched lipid chains are also part of phosphomycoketides;long-chain lipids of polyketide origin found in Mycobacterium tuberculosis.…”