Synthesis of the B-seco limonoid scaffold

Schuster, Hannah; Martinez, Rémi; Bruss, Hanna; Antonchick, Andrey P.; Kaiser, Markus; Schürmann, Markus; Waldmann, Herbert

doi:10.1039/c1cc11388g

Cited by 18 publications

(11 citation statements)

References 19 publications

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“…2.1.2. Synthesis of (+)-zeylenone QA-6 was accomplished according to the literature in 44.3 % yield (Scheme 2) [14,16]. The following sharpless dihydroxylation of QA-6 was tried by potassium osmate without chiral ligands, but yielded the QA-7 and QA-7' with a ratio of 1:0.6 calculated by 1 HNMR(Scheme 3, Table 1).…”

Section: Total Synthesis Of (+)-Zeylenonementioning

confidence: 99%

Concise Total Synthesis of (+)-Zeylenone with Antitumor Activity and Structure-Activity Relationship of Its Derivatives

Sun¹,

Yang²,

Xu³

et al. 2019

Preprint

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(-)-Zeylenone is a promising cytotoxic agent，which is a natural product isolated from Uvaria grandiflora Roxb. Though substantial antitumor mechanism has been researched , little has focused on its enantiomer (+)-Zeylenone.This article will try to find a gram scale synthesis method of (+)-Zeylenone and explain the structure-activity relationship of this kind of compound. Total synthesis of (+)-zeylenone was completed in 13 steps with quinic acid as starting material in 8.8% overall yield. The highlight of the route was the control of the three carbon’s chirality by clever use of single step dihydroxylation under the direction of the key C-3 chirality. In addition, zeylenone derivatives were designed and synthesized and their antitumor activity were evaluated against three human cancer cell lines using the CCK8 assay. Structure-activity relationship suggested compounds with both two absolute configurations exhibited good activity. Besides, hydroxyls at C-1/2 position were crucial for the activity and esterification of C-1 hydroxyl with large groups made the activity disappeared. Hydroxyl at C-3 position was also important as proper ester substituent could increase the potency.

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Section: Total Synthesis Of (+)-Zeylenonementioning

confidence: 99%

Concise Total Synthesis of (+)-Zeylenone with Antitumor Activity and Structure-Activity Relationship of Its Derivatives

Sun¹,

Yang²,

Xu³

et al. 2019

Preprint

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“…In this paper we present a full report on this synthesis [36] as well as further synthetic studies towards the application of the developed strategy to the total synthesis of B- seco limonoid natural products.…”

Section: Introductionmentioning

confidence: 99%

“…Taking into account the biology-oriented synthesis (BIOS) concept [ 27 – 34 ], which employs the scaffolds of biologically relevant natural product classes to inspire the synthesis of probes and reagents for chemical biology and medicinal chemistry research, we aimed at the development of a synthetic strategy to get access to the B- seco limonoid scaffold by means of a [3,3]-sigmatropic rearrangement as key step enabling the formation of the crucial C9–C10 bond ( Scheme 1 ) [ 35 ]. In this paper we present a full report on this synthesis [ 36 ] as well as further synthetic studies towards the application of the developed strategy to the total synthesis of B- seco limonoid natural products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the B-seco limonoid core scaffold

Bruss¹,

Schuster²,

Martinez³

et al. 2014

Beilstein J. Org. Chem.

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SummarySynthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems.

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“…Williams and co-workers recently completed a total synthesis of mexicanolide ( 3 ) through employment of an analogous 1,6-conjugate addition strategy. 11 Additionally, a relay synthesis of azadirachtin reported by Ley took advantage of the availability of this natural product from neem oil. 12 …”

mentioning

confidence: 99%

Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

Schuppe

Newhouse

2017

J. Am. Chem. Soc.

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We report the first total synthesis of the limonoid andirolide N using a 12-step sequence from commercially available materials. The final step of this route demonstrates the chemical feasibility of our biosynthetic proposal that andirolide N arises from 8α-hydroxycarapin. The strategic use of a degraded limonoid as a platform for the synthesis of more structurally complex congeners may be a general approach to obtain limonoids with diverse functional properties.

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Synthesis of the B-seco limonoid scaffold

Abstract: The underlying stereochemically complex and densely functionalized scaffold of the B-seco limonoids was synthesized employing an Ireland-Claisen rearrangement as key transformation.

Cited by 18 publications

References 19 publications

Concise Total Synthesis of (+)-Zeylenone with Antitumor Activity and Structure-Activity Relationship of Its Derivatives

Concise Total Synthesis of (+)-Zeylenone with Antitumor Activity and Structure-Activity Relationship of Its Derivatives

Synthesis of the B-seco limonoid core scaffold

Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

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