Tetrahedron Letters p. 1019 - 1022 (1996)
Update date:2022-08-03
Topics:
Delpech, Bernard
Calvo, Daniel
Lett, Robert
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.
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