Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 20, Pages 14826-14830Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01729
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A new approach to construct the tricyclic framework of the diterpenoid vinigrol is described. The challenging 1,5-butanodecahydronaphthalene core was efficiently and diastereoselectively established through a combination of type II [5 + 2] cycloaddition and Wolff rearrangement. In addition, a formal total synthesis of (-)-vinigrol was achieved in 12 steps, in which Baran's intermediate was efficiently produced from a known compound by a two-step sequence involving a stereoselective alpha-hydroxylation and a diastereoselective alpha-ketol rearrangement.
A new approach to construct the tricyclic framework of the diterpenoid vinigrol is described. The challenging 1,5-butanodecahydronaphthalene core was established efficiently and diastereoselectively through a combination of type II [5 + 2] cycloaddition and Wolff rearrangement. In addition, a formal total synthesis of (-)-vinigrol was achieved in 12 steps, in which Baran's intermediate was efficiently produced from a known compound by a two-step sequence involving a stereoselective alpha-hydroxylation and a diastereoselective alpha-ketol rearrangement.
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