Diastereoselective addition of organozinc reagents to 2-alkyl-3-(arylsulfanyl)propanals

Larsson, Michael; Galandrin, Elodie; Högberg, Hans‐Erik

doi:10.1016/j.tet.2004.09.005

Cited by 10 publications

(1 citation statement)

References 34 publications

(14 reference statements)

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“…The diastereomeric ratio of 6 was determined as 1.3:1 by integration of O -methine protons at δ 3.62 and 3.55 (Figure S1), with a similar ratio observed for 11 . Comparison of the chemical shifts and coupling constants of O -methine protons in 6 and 11 with literature values for (2 R *,3 S *)- and (2 R *,3 R *)-3-methyltridecan-2-ol (Larsson, et al, 2004) showed that the major isomer in both 6 and 11 had a 10 R *,11 S * relative configuration. Initially, upon isolation we thought that this was likely due to partial racemization at the OH-bearing C-11 position, but the Mosher’s analysis described above revealed that only single C-11 isomers were present (Figure S2).…”

Section: Resultsmentioning

confidence: 71%

A Bacterial Source for Mollusk Pyrone Polyketides

Lin

Torres

Ammon

et al. 2013

Chemistry & Biology

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Summary In the oceans, toxic secondary metabolites often protect otherwise poorly defended, soft-bodied invertebrates such as shell-less mollusks from predation. The origins of these metabolites are largely unknown, but many of them are thought to be made by symbiotic bacteria. In contrast, mollusks with thick shells and toxic venoms are thought to lack these secondary metabolites due to reduced defensive needs. Here, we show that heavily defended cone snails also occasionally contain abundant secondary metabolites, γ-pyrones known as nocapyrones, and that these pyrones are synthesized by symbiotic bacteria. This study shows that symbiotic bacteria can produce metabolites isolated from gastropod mollusks. The symbiotic bacteria, Nocardiopsis alba CR167, are closely related to potentially widespread actinomycetes that we propose to be casual symbionts of invertebrates on land and in the sea. The natural roles of nocapyrones are not known, but they are active in neurological assays at low micromolar levels, revealing that mollusks with external shells are an overlooked source of secondary metabolite diversity.

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Section: Resultsmentioning

confidence: 71%

A Bacterial Source for Mollusk Pyrone Polyketides

Lin

Torres

Ammon

et al. 2013

Chemistry & Biology

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Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

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The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

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