Skip to main content
. Author manuscript; available in PMC: 2020 Jan 31.
Published in final edited form as: Nat Chem. 2017 Jun 19;9(10):944–949. doi: 10.1038/nchem.2801

Figure 5 |. Radical cyclization and first generation total synthesis of tubingensin B.

Figure 5 |

Radical cyclization precursor 19 was prepared using several functional group manipulations. In turn, the radical cyclization led to the efficient assembly of the [3.2.2]nonane core and provided bicycle 20. Following further manipulations, 1 was obtained, albeit with its C19 epimer forming predominantly in the final step. MOM, methoxymethyl; THF, tetrahydrofuran; TIPSOTf, triisopropylsilyl trifluoromethanesulfonate; AIBN, azobisisobutyronitrile; TBAF, tetrabutylammonium fluoride; DMP, Dess–Martin Periodinane; BINAP, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.