Synthetic Studies toward the Revised Aglycone of Mandelalide A

AnkiReddy, Praveen; Sandeep, AnkiReddy; Sabitha, Gowravaram

doi:10.1002/slct.201601076

Cited by 4 publications

(4 citation statements)

References 33 publications

(9 reference statements)

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“…Subsequently, Fürstner confirmed this revision by total synthesis of 5 , and in turn predicted similar revisions for mandelalides B–D ( 6 – 8 , Figure ). , Total syntheses of the revised structure of (−)-mandelalide A ( 5 ) have also been reported by several research groups, including our laboratory …”

Section: Introductionmentioning

confidence: 59%

“…Results from that study demonstrated that the glycosylated mandelalides are effective site-specific inhibitors of mitochondrial function in living cells, and that cells with an oxidative phenotype are most sensitive to mandelalide-induced decreases in cell proliferation and viability. Notably, the synthetic work from our laboratory and others ,, has illustrated the indispensable role of organic synthesis in natural products chemistry for proof of structure and to supply material for biological investigation. Herein we record a full account of our synthetic venture that exploits Anion Relay Chemistry to access the A-type members of the mandelalide family, comprising (−)-mandelalides A and L ( 5 and 16 ), the two most potent members of the family.…”

Section: Introductionmentioning

confidence: 98%

“…Interestingly, inconsistent results for the cytotoxic efficacy of synthetic (−)-mandelalide A ( 5 ) were reported by several investigators, noting weak or disappointing biological activity against a small panel of cancer cell lines. ,, Subsequently, recollection of the rare tunicate source by McPhail and co-workers (2013) led to additional natural congeners, mandelalides E–L ( 9 – 16 , Figure ) that facilitated further evaluation of the bioactivity of the mandelalide family . The newly characterized members of the mandelalide family were classified into three different structural types (Types A–C, Figure ), based on three different macrocyclic motifs associated with the prototype structures of mandelalides A–C.…”

Section: Introductionmentioning

confidence: 99%

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Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy

et al. 2018

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The mandelalides comprise a family of structurally complex marine macrolides that display significant cytotoxicity against several human cancer cell lines. Presented here is a full account on the development of an Anion Relay Chemistry (ARC) strategy for the total synthesis of (-)-mandelalides A and L, the two most potent members of the mandelalide family. The design and implementation of a three-component type II ARC/cross-coupling protocol and a four-component type I ARC union permits rapid access respectively to the key tetrahydrofuran and tetrahydropyran structural motifs of these natural products. Other highlights of the synthesis include an osmium-catalyzed oxidative cyclization of an allylic 1,3-diol, a mild Yamaguchi esterification to unite the northern and southern hemispheres, and a late-stage Heck macrocyclization. Synthetic mandelalides A and L displayed potent cytotoxicity against human HeLa cervical cancer cells (EC, 1.3 and 3.1 nM, respectively). This synthetic approach also provides access to several highly potent non-natural mandelalide analogs, including a biotin-tagged mandelalide probe for future biological investigation.

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Section: Introductionmentioning

confidence: 59%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy

et al. 2018

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“…Amos B. Smith developed an anion relay chemistry (ARC) strategy [74] to synthesize the tetrahydrofuran and tetrahydropyran structural motifs which were joined by Yamaguchi esterification [75]. Intramolecular Heck cyclization [76], Sharpless asymmetric dihydroxylation [77] or Julia olefination [78] were also employed in other total syntheses.…”

Section: Mandelalidesmentioning

confidence: 99%

The Tetrahydrofuran Motif in Polyketide Marine Drugs

et al. 2022

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Oxygen heterocycles are units that are abundant in a great number of marine natural products. Among them, marine polyketides containing tetrahydrofuran rings have attracted great attention within the scientific community due to their challenging structures and promising biological activities. An overview of the most important marine tetrahydrofuran polyketides, with a focused discussion on their isolation, structure determination, approaches to their total synthesis, and biological studies is provided.

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Still–Gennari Olefination and its Applications in Organic Synthesis

Janicki

Kiełbasiński

2020

Adv Synth Catal

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The Still–Gennari olefination is a widely applied modification of the Horner–Wadsworth–Emmons reaction, allowing access to Z‐olefins by carbonyl group transformation. Its synthetic utility is undoubtedly of great significance for organic chemistry, as can be illustrated by the number of citations of the original report by W. C. Still and C. Gennari which up to date has been cited over 1000 times. In 2008 Nobel prize winner Ei‐ichi Negishi indicated the Still–Gennari olefination as one of the crucial methods for tolefin synthesis, complementary to palladium‐catalyzed alkenylations. Surprisingly, so far there is no review concerning this popular and valuable transformation. Therefore, we aim to comprehensively systematize achievements in this field and to present the scope of applications of the Still–Gennari olefination along with recent examples in the total synthesis of biologically active compounds. Our review is intended to be of interest for the general chemical community as well as to be a helpful source of information for synthetic organic chemists.magnified image

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Synthetic Studies toward the Revised Aglycone of Mandelalide A

Cited by 4 publications

References 33 publications

Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy

Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy

The Tetrahydrofuran Motif in Polyketide Marine Drugs

Still–Gennari Olefination and its Applications in Organic Synthesis

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