132620-06-5Relevant articles and documents
A Radical-Polar Crossover Annulation to Access Terpenoid Motifs
Thomas, William P.,Schatz, Devon J.,George, David T.,Pronin, Sergey V.
supporting information, p. 12246 - 12250 (2019/08/27)
A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.
Total synthesis of forskolin - Part II
Delpech, Bernard,Calvo, Daniel,Lett, Robert
, p. 1019 - 1022 (2007/10/03)
The further elaboration of the key-intermediate 5 into forskolin 1 has been achieved via two different routes. Key features of this new total synthesis are: 1) the stereospecific formation of the 6β, 7β, 8α-triol via the BF3-Et2O assisted opening of the epoxy carbamate 8; 2) use of the 8α, 11-di-t-butylsilylene ketal for the specific protection of the 6β, 7β-diol, from the tetrol 10(A); two new sequences for the formation of the dihydro-γ-pyrone ring in high overall yield from 23; 4) the stereoselective divinyl cuprate conjugate α-addition on the dihydro-γ-pyrone 16 or 28, in the presence of BF3-Et2o, with the stereochemistry required for forskolin synthesis.
A total synthesis of (±)-forskolin
Hashimoto,Sakata,Sonegawa,Ikegami
, p. 3670 - 3672 (2007/10/02)
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