Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and <i>syn</i>-Selective Vinylogous Aldol Chemistry

Lisboa, Marilda P.; Jones, David M.; Dudley, Gregory B.

doi:10.1021/ol400014e

Cited by 33 publications

(17 citation statements)

References 43 publications

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“…To date, three total syntheses [116,117,118,119,120] of palmerolide A have been reported. Four groups disclosed formal syntheses [121,122,123,124,125,126], and various synthetic approaches have also been described [127,128,129,130,131,132,133,134,135]. The synthesis of the reported structure of palmerolide C has also been achieved, and a structural revision has been proposed [136].…”

Section: Tunicatesmentioning

confidence: 99%

Secondary Metabolites from Polar Organisms

Tian

Zhao

2017

Marine Drugs

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Polar organisms have been found to develop unique defences against the extreme environment environment, leading to the biosynthesis of novel molecules with diverse bioactivities. This review covers the 219 novel natural products described since 2001, from the Arctic and the Antarctic microoganisms, lichen, moss and marine faunas. The structures of the new compounds and details of the source organism, along with any relevant biological activities are presented. Where reported, synthetic and biosynthetic studies on the polar metabolites have also been included.

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Section: Tunicatesmentioning

confidence: 99%

Secondary Metabolites from Polar Organisms

Tian

Zhao

2017

Marine Drugs

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“…92). 97 They utilized the same aldehyde (232), that the De Brabander and Nicolaou groups used in their total syntheses of palmerolide A (231), as described above. However, Dudley et al were able to obtain the desired 4,5-syn-conguration, needed for palmerolide A (231), directly in the vinylogous Mukaiyama aldol reaction with 69% yield without the need to invert the conguration at C4-hydroxy group.…”

Section: Syn-selective Kobayashi Vmarmentioning

confidence: 99%

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

et al. 2014

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The vinylogous Mukaiyama aldol reaction (VMAR) allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di and tri-substituted double bonds in one single operation. In this review, we will highlight stereoselective protocols that have been used in natural product synthesis and cluster them into the four groups that can be obtained from different silyl ketene acetals or enol ethers. At the beginning, an overview on different stereoselective VMARs is presented; disregarding their applications in total syntheses.

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“…Recently, Dudley and colleagues synthesized a twenty-membered lactone palmerolide A by coupling acid and alcohol subunits. 9 …”

Section: (D) Synthesis Of Palmerolide Amentioning

confidence: 99%

2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent)

Kotammagari

2014

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research spotlight 2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent) Compiled by Tharun Kumar KotammagariTharun Kumar Kotammagari was born in Andhra Pradesh state, India. He received his M.Sc. degree in organic chemistry from Jawaharlal Nehru Technological University, Anantapur. He is currently working towards his Ph.D. degree at the Division of Organic Chemistry of CSIR-National Chemical Laboratory, Pune, India under the supervision of Dr. Asish K. Bhattacharya. His research is focused on the synthesis of bioactive natural products, isolation and structure elucidation of biologically active secondary metabolites and development of new synthetic methodologies.

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Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and syn-Selective Vinylogous Aldol Chemistry

Cited by 33 publications

References 43 publications

Secondary Metabolites from Polar Organisms

Secondary Metabolites from Polar Organisms

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent)

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