Biomimetic total synthesis of gracilioethers B and C

Matthew Norris; Michael Perkins; Erik Sorensen

doi:10.1021/ol503695j

Biomimetic total synthesis of gracilioethers B and C

Matthew Norris, Michael Perkins, Erik Sorensen

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Total syntheses of the marine polyketide metabolites gracilioethers B and C have been realized in 9 steps (40% overall yield) and 10 steps (34% overall yield), respectively. The [2(5H)-furanylidene]ethanoate (furanylidene) motif was constructed in a transacetalization/dehydration cascade of an advanced β-ketoester intermediate, which was designed to mimic a postulated biosynthetic precursor to the natural products. The relative and absolute configurations of gracilioethers B and C are confirmed as (6R,8R) and (6R,8R,11S), respectively.

Original language	English
Pages (from-to)	668-671
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/ol503695j
Publication status	Published - 6 Feb 2015

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author = "Matthew Norris and Michael Perkins and Erik Sorensen",

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AU - Perkins, Michael

AU - Sorensen, Erik

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JO - Organic Letters

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ER -

Biomimetic total synthesis of gracilioethers B and C

Abstract

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