Total synthesis of forskolin — Part II

阅读量:

28

作者:

B DelpechDaniel Calvo +R Lett

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摘要:

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 BF 3 Et 2 O 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 BF 3 Et 2 O, with the stereochemistry required for forskolin synthesis.

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DOI:

10.1016/0040-4039(95)02364-X

被引量:

107

年份:

1996

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来源期刊

Tetrahedron Letters
12 February 1996

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2006
被引量:20

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