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An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product
Jayasinghe, Susanthi Venukadasula, Phanindra K. M. Hanson, Paul R.
Jayasinghe, Susanthi
Venukadasula, Phanindra K. M.
Hanson, Paul R.
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Abstract
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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2014-01-03
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American Chemical Society
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Jayasinghe, S., Venukadasula, P. K. M., & Hanson, P. R. (2014). An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product. Organic Letters, 16(1), 122–125. http://doi.org/10.1021/ol403110p