Correction: Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one

Abstract

Correction for ‘Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one’ by Dattatraya H. Dethe et al., Chem. Commun., 2024, 60, 7866–7869, https://doi.org/10.1039/D4CC01982B.

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The authors regret that Schemes 2 and 3 in the original article incorrectly showed mirror images of the molecular structures. The corrected Schemes 2 and 3 are provided below. The supplementary information file for the original article also contained incorrect mirror images, which have now been corrected in an updated version.

Scheme 2 Retrosynthetic analysis.

Scheme 3 Total synthesis of (+)-16α, 17-dihydroxy-atisan-3-one, (+)-sapinsigin H and (+)-agallochaol C. Reagent and conditions: (a) NaHMDS (1.9 M, 1.1 equiv.), PhNTf₂ (1.1 equiv.), THF, −78 °C, 4 h, 95%; (b) Pd(OAc)₂ (10 mol%), methyl acrylate (10.0 equiv.), Et₃N (10.0 equiv.), PPh₃ (0.1 equiv.), 95 °C, 14 h, 95%; (c) LiOH (6.0 equiv.), THF/MeOH/H₂O (3 : 1 : 2), rt, 12 h, 88%; (d) propionic anhydride, 180 °C, 2 days, 80%; (e) HNC(N(CH₃)₂)₂ (1.05 equiv.), PIDA (2.4 equiv.), MeOH, −7 °C, 4 h; (f) CH₂CH₂ (40 bar), toluene, 110 °C, 24 h, 40% (2 steps); (g) SmI₂, THF/MeOH (5: 1), rt, 30 min, 85%; (h) H₂, 10% Pd/C, EtOAc, rt, overnight, 92%; (i) PPh₃MeBr (3.0 equiv.), KOt-Bu (2.0 equiv.), THF, 0 °C to rt, 2 h, 91%; (j) LiAlH₄ (1.0 equiv.), THF, 0 °C to rt, 1 h, 95%; (k) DMP (1.2 equiv.), NaHCO₃ (8.0 equiv.), CH₂Cl₂, rt, 1 h, 95%; (l) OsO₄ (2.5 wt% in t-BuOH, 0.20 equiv.), NMO (2.0 equiv.), THF/t-BuOH/H₂O (1 : 1 : 0.2), rt, 30 h, 90%; (m) Ac₂O (3.0 equiv.), Et₃N (5.0 equiv.), CH₂Cl₂, rt, 24 h, separable diastereomers 22 (57%), 23 (42%); (n) K₂CO₃ (2.0 equiv.), MeOH, rt, 1 h, 90%; (o) KOt-Bu (7.0 equiv.), t-BuOH, O₂, rt, 4 h, 95%; (p) mCPBA (1.5 equiv.), NaHCO₃ (5.0 equiv.), 0 °C, 1 h, 65%; (q) pTSA, CH₂Cl₂, rt, 8 h, 75%; (r) K₂CO₃ (2.0 equiv.), MeOH, rt, 1 h, 90%.

The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.

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Footnote

† These authors contributed equally

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