Biomimetic total synthesis of gracilioethers B and C

Matthew D. Norris; Michael V. Perkins; Erik J. Sorensen

doi:10.1021/ol503695j

Biomimetic total synthesis of gracilioethers B and C

Matthew D. Norris, Michael V. Perkins, Erik J. Sorensen

Chemistry

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

18 Scopus citations

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 (US)
Pages (from-to)	668-671
Number of pages	4
Journal	Organic letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/ol503695j
State	Published - Feb 6 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503695j

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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.",

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AU - Perkins, Michael V.

AU - Sorensen, Erik J.

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AB - 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.

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Biomimetic total synthesis of gracilioethers B and C

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