A short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A &amp; B, hamabiwalactone B and ancepsenolide

Vasamsetty, Laxmaiah; Khan, Faiz Ahmed; Mehta, Goverdhan

doi:10.1016/j.tet.2015.04.009

“…Indeed, 8 has not yet been reported to undergo Suzuki-Miyaura cross-couplings with pinacol boronates; only (less sterically hindered) boronic acids have been utilized as coupling partners. 15,16 We therefore hydrolyzed pinacol boronate 9 to the boronic acid as reported by Mehta 17 and were gratified to see that boronic acid 14 successfully underwent coupling with 8 to afford (Z,E)-dienyl MIDA boronate 13 (Scheme 4). Boronic acid 10 was coupled with 8 in a similar fashion to give dienyl MIDA boronate 15.…”

Section: Resultsmentioning

confidence: 99%

“…A mixture of crude boronic acid 14 (101.65 mg, 0.434 mmol), 17 cis-2-bromovinylboronic acid MIDA ester (114.8, 0.439 mmol), Cs 2 CO 3 (426.7 mg, 1.31 mmol) and XPhos Pd G2 (34.1 mg, 0.043 mmol) was evacuated and then placed under a nitrogen atmosphere. THF (2.5 mL) was added and the mixture was stirred for 22 hours.…”

Section: ((1z3e)-6-((tert-butyldimethylsilyl)oxy)hexa-13-dien-1-yl)mentioning

confidence: 99%

Concise, diastereoconvergent synthesis of endiandric-type tetracycles by iterative cross coupling

Go

¹

,

Wetzler

²

,

Kim

³

et al. 2016

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on the occasion of his receiving the Tetrahedron Young Investigator Award Both fused and bridged tetracyclic scaffolds characteristic of endiandric acid-type natural products have been prepared in just seven steps each (longest linear sequence) from Burke's commercial cis-2-bromovinylboronic acid MIDA ester. Three iterative Suzuki-Miyaura couplings using MIDA boronates, including the first such example of a Z-Z coupling, trigger an 8/6-electrocyclization cascade. The mixture of endo and exo bicycles thus formed are elaborated into tetracycles via Horner-Wadsworth-Emmons and Diels-Alder reactions. In the process, the endo and exo diastereomers interconvert to ultimately deliver the desired products.

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Biosynthesis of Pseudomonas‐Derived Butenolides

Klapper

¹

,

Schlabach

²

,

Paschold

³

et al. 2020

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Butenolides are well‐known signaling molecules in Gram‐positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram‐negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagenesis, heterologous expression, and identification of key shunt and intermediate products were crucial to propose a biosynthetic pathway for both Pseudomonas‐derived butenolides. Comparative transcriptomics suggests a link between styrolide formation and the regulatory networks of the bacterium.

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Biosynthesis of Pseudomonas‐Derived Butenolides

Klapper

¹

,

Schlabach

²

,

Paschold

³

et al. 2020

View full text Add to dashboard Cite

Butenolides are well‐known signaling molecules in Gram‐positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram‐negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagenesis, heterologous expression, and identification of key shunt and intermediate products were crucial to propose a biosynthetic pathway for both Pseudomonas‐derived butenolides. Comparative transcriptomics suggests a link between styrolide formation and the regulatory networks of the bacterium.

show abstract

A short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide

Cited by 9 publications

References 72 publications

Concise, diastereoconvergent synthesis of endiandric-type tetracycles by iterative cross coupling

Concise, diastereoconvergent synthesis of endiandric-type tetracycles by iterative cross coupling

Biosynthesis of Pseudomonas‐Derived Butenolides

Biosynthesis of Pseudomonas‐Derived Butenolides

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