Neoisostegane, a New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia araliacea

Taafrout, M; Rouessac, F.; Robin, Jean‐Pierre; Hicks, Rickey P.; Shillady, Donald D.; Sneden, Albert T.

doi:10.1021/np50034a005

Cited by 20 publications

(22 citation statements)

References 10 publications

(29 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Achiwa and co-workers developed a catalytic enantioselective hydrogenation of a-arylidenesuccinic acid half ester 140 en route to the stereoselective total syntheses of three naturally occurring lignans: (þ)-collinusin, (À)-deoxypodophyllotoxin, 226 and (þ)-neoisostegane (Scheme 29.9). 226,227 The enantioselective hydrogenations of 140 were carried out at 30 C for 40 hours in methanol in the presence of Et 3 N under 1 atm of hydrogen using 0.2 mol% of a neutral Rh(I)-complex as a precatalyst, which was prepared in situ from (S,S)-MOD-DIOP and 1/2[Rh(COD)Cl] 2 in methanol. 228 After the workup, hydrogenation product (R)-141 was obtained in almost quantitative yields and enantioselectivity (up to 93-95% ee).…”

Section: Rhodium-catalyzed Stereoselective Hydrogenation Of Functionamentioning

confidence: 99%

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

View full text Add to dashboard Cite

Asymmetric homogeneous hydrogenation is perhaps one of the most researched areas in homogeneous catalysis; thus, it is now used in numerous innovative applications in stereoselective syntheses of many chiral pharmaceutical and natural products. Metal complexes, derived from transition metals, like Rh, Ru, Ir, and so on, and chiral ligands (usually mono‐ or diphosphine ligands), are widely used as catalysts in asymmetric alkene hydrogenation as a result of their efficiency in the preparation of enantiopure compounds with excellent atom economy. This chapter provides many interesting examples of homogeneous enantio‐ and diastereoselective hydrogenation of CC bonds, highlighting the utility of these methods as useful synthetic tools for the construction of stereogenic centers in stereoselective drug and natural product syntheses.

show abstract

Section: Rhodium-catalyzed Stereoselective Hydrogenation Of Functionamentioning

confidence: 99%

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

View full text Add to dashboard Cite

show abstract

“…Both compounds were found in the extracts of steganotaenia araliacea 26,27 but interestingly possess the opposite axial chirality. 26,28 Most probably the substitution in C5 position (see Figure 2, structures 3 and 4) defines the different alignment for the cyclization step in case of steganacine's biosynthesis. Another lignan natural product is (-)--conidendrin (8).…”

Section: Introductionmentioning

confidence: 99%

TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (−)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane

et al. 2019

View full text Add to dashboard Cite

The asymmetric allylation under the assistance of catalytic amounts of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (TRIP) allows the concise construction of the lignan scaffold from simple aldehydes and allylic bromides with full control of the two formed stereocenters. This young methodology has been employed to synthesize four naturally and pharmaceutically active lignans. Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene classes have been synthesized in 40–47% overall yield along four-step synthetic routes.

show abstract

“…In 1973 Kupchan et al reported the presence of antileukemic lignan lactones in Steganotaenia araliacea of Ethiopian origin [5]. Over the next 20 years there was extensive activity to investigate the structure of related lignans and saponins, mostly in those from Steganotaenia araliacea of West African origin [6]- [15]. In addition, these structural studies stimulated a flurry of synthetic chemistry [16]- [19].…”

Section: Introductionmentioning

confidence: 99%

GC-MS Analysis of the Essential Oil and Methanol Extract of the Seeds of Steganotaenia araliacea Hochst

Demoz¹,

Gachoki²,

Mungai³

et al. 2014

AJPS

View full text Add to dashboard Cite

Background: Steganotaenia araliacea is a multipurpose plant and has wider applications in the folklore for the treatment of various ailments. Previously the presence of antileukemic lignan lactones and saponins was detected in the stem bark, root and leaf of Steganotaenia araliacea. Besides, the diuretic and antibacterial activities of the plant were reported. However, there has been no attempt to examine the constituents of the seeds of Steganotaenia araliacea. This paper reports the first such study of both the essential oil and methanol extract of the seeds of the plant. Methods: The seeds of the plant were shade dried, pounded and thus extracted using methanol. Besides, the essential oil of the seeds was collected using steam distillation. The components of the methanol extract were studied both by GC-MS and preliminary phytochemical studies; the essential oil was running on GC-MS for analysis. Results: The GC-MS analysis of the essential oil of the seeds identified the presence of α-linalool, α-pinene, m-cresol, p-menth-1-en-4-ol, p-menth-1-en-8-ol, myristicin and others. Besides, the methanol extract of the seeds showed the presence of falcarinol, apiol, scoparone, stigmasterol, myristicin etc. The preliminary phytochemical analysis of the methanol extract of the seeds confirms the presence of alkaloids, flavonoids, tannins, coumarines, steroids, and phenols. Conclusion: This plant contains bioactive metabolites and thus can be used as an alternative and complementary medicine in treatment of different ailments. However, further studies on the bioactivity and toxicity of the plant should be done.

show abstract

Neoisostegane, a New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia araliacea

Cited by 20 publications

References 10 publications

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (−)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane

GC-MS Analysis of the Essential Oil and Methanol Extract of the Seeds of Steganotaenia araliacea Hochst

Contact Info

Product

Resources

About