Chemoenzymatic and enantioselective assembly of the (1α,3aβ,6α,7aβ)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: validation of a new synthetic strategy and the identification of enantiomeric switching regimes

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

“…We have since reported extensions of these protocols to total or formal total syntheses of phellodonic acid ( 112 ), (−)‐connatusin A ( 113 ), (+)‐connatusin B ( 114 ), (−)‐hypnophilin ( 115 ) and (−)‐coriolin ( 116 ). A route to the octahydro‐1,6‐methano‐1 H ‐indene framework associated with the marine sesquiterpenoid 2‐isocyanoallopupukeanane ( 117 ) has established by related means …”

Syntheses and biological studies of marine terpenoids derived from inorganic cyanide

“…Even though this level of detail yields large schemes, the larger format allows for the laboriousness of a sequence to be appreciated and also serves an educational role: learning many reactions (and how to avoid using so many!). Not every synthesis is covered; the remaining syntheses and relevant synthesis studies may be found in references lxvii–lxxxiii.…”

Accessing the antipodal series in microbial arene oxidation: a novel diene rearrangement induced by tricarbonyliron(0) complexation

“…Our approach is complementary to other strategies reported previously for achieving this ''enantiomeric switch''. For example, substituted iodobenzenes can undergo 2,3-dihydroxylation followed by reductive iodine removal, 20,22 but this can preclude the use of diol derivatives possessing reductively labile functionality. The conceptually distinct approach of enantiodivergent synthesis has also been employed, 21,22 requiring that two different synthetic routes be established.…”

“…For example, substituted iodobenzenes can undergo 2,3-dihydroxylation followed by reductive iodine removal, 20,22 but this can preclude the use of diol derivatives possessing reductively labile functionality. The conceptually distinct approach of enantiodivergent synthesis has also been employed, 21,22 requiring that two different synthetic routes be established. In contrast, the approach we describe utilises only oxidative conditions and will permit access to both enantiomers of a given target by the same synthetic pathway.…”