An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.
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用于合成 (+)-strictifolione 和相关天然产物的高效、模块化方法。

DOI:
10.1021/ol403110p
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发表时间:
2014-01-03
期刊:
影响因子:
5.2
通讯作者:
Hanson, Paul R.
Hanson, Paul R.
中科院分区:
化学1区
文献类型:
--
作者:
Jayasinghe, Susanthi;Venukadasula, Phanindra K. M.;Hanson, Paul R.

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An efficient, library amenable, “pot economical” total synthesis of (+)-strictifolione and the related natural product, (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyrone are reported. This modular approach takes advantage of two consecutive phosphate tether-mediated, one-pot, sequential protocols, followed by a final cross metathesis to deliver both antifungal natural products in a three-pot process from the respective enantiomeric (R,R)- and (S,S)-trienes with minimal purification. A salient feature of this route is that additional protecting groups are not required as a result of the orthogonal protecting- and leaving-group properties innate to phosphate triesters.
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