Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis.

Matthew Katcher, Timothy F Jamison

Abstract read

In one paragraph

Article in Tetrahedron, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes.Organic letters · 2019
Article

4 · The record

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PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors.

Matthew KatcherDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139 USA.

Timothy F JamisonDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139 USA.

Funding

Synthetic Strategies based on expoxide coupling reactionsR01GM072566 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI JAMISON, TIMOTHY F · 2005 to 2017

$3.1M

A Cascade Reaction to Synthesize Ladder Polyethers with 1,3 Diaxial Methyl GroupsF32GM108181 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI KATCHER, MATTHEW HERMAN · 2014 to 2016

$123k

NIGMS NIH HHS F32 GM108181NIGMS NIH HHS R01 GM072566

6 · The paper itself

Abstract

Shortly after the initial isolation of marine ladder polyether natural products, biomimetic epoxide-opening cascade reactions were proposed as an efficient strategy for the synthesis of these compounds. However, difficulties in assembling the cascade precursors have limited the realization of these cascades. In this report, we describe strategies that provide convergent access to cascade precursors via regioselective allylation and efficient fragment coupling. We then investigate epoxide-opening cascades promoted by strong bases for the formation of fused tetrahydropyrans. These strategies are evaluated in the context of the synthesis of rings CDEFG of brevisulcenal F.

Indexed as

Cascade reactionsEpoxide openingsNatural productsOxygen heterocyclesPolyethers

Identifiers

PMID29479119

DOI10.1016/j.tet.2018.01.039

PMCPMC5823242

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