Efficient Construction of the Clerodane Decalin Core by an Asymmetric Morita–Baylis–Hillman Reaction/Lewis Acid Promoted Annulation Strategy

Rodgen, Stacy A.; Schaus, Scott E.

doi:10.1002/anie.200601076

Cited by 55 publications

(12 citation statements)

References 43 publications

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“…Efficient construction of the clerodane decalin core of asmarines A and B has been achieved by an asymmetric Morita-Baylis-Hillman reaction/Lewis acid-promoted annulation strategy [86]. The tetrahydrodiazepinopurine ring skeleton 5 was prepared employing the ring-closing metathesis reaction on Boc-protected 6-allylamino-7-(propen-1-yl)purine 6 as the key step for the construction of the seven-membered ring.…”

Section: Sources Of Agelasines Asmarines and Related Compoundsmentioning

confidence: 99%

“…The cyclization modes for 9-mono and 9,9-disubstituted tetra-hydro[1,4]diazepino[1,2,3- g , h ]purine structure can form the basis of SAR studies of asmarine analogs, and provide a route for the total synthesis of asmarine A starting from the appropriate diterpene and purine [36]. The biological target of asmarine A and B is not known [86]. …”

Section: Biological Activity Of Marine Terpenyl-purine Alkaloidsmentioning

confidence: 99%

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Terpenyl-Purines from the Sea

Gordaliza

2009

Marine Drugs

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Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity against a variety of species, including Mycobacterium tuberculosis, and also an important cytotoxic activity against several cancer cell lines, including multidrug-resistant ones. Of particular interest in this context are the asmarines (tetrahydro[1,4]diazepino[1,2,3-g,h]purines), which have shown potent antiproliferative activity against several types of human cancer cell lines. This review summarizes the sources of isolation, chemistry and bioactivity of marine alkylpurines and their bioactive derivatives.

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Section: Sources Of Agelasines Asmarines and Related Compoundsmentioning

confidence: 99%

Section: Biological Activity Of Marine Terpenyl-purine Alkaloidsmentioning

confidence: 99%

Terpenyl-Purines from the Sea

Gordaliza

2009

Marine Drugs

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“…The clerodane class of natural products is diterpenes that exhibit potent antiproliferative activity against several types of human-cancer-cell lines. Schaus et al formulated an asymmetric synthetic protocol toward the synthesis of clerodane decalin core of asmarine via a two-step ring-annulation procedure [95]. The first step of the synthesis to construct the core of clerodane was the asymmetric MBH reaction of cyclohexenone 245 with aldehydes 343 promoted by Et 3 P and binapthol-derived Brønsted acids whereas the second step involved BF 3 .OEt 2 -catalyzed intramolecular Hosomi-Sakauri reaction as outlined in Scheme 54.…”

Section: Clerodane Decalin Corementioning

confidence: 99%

Applications of Morita-Baylis-Hillman Reaction to the Synthesis of Natural Products and Drug Molecules

Bhowmik¹,

Batra

2015

COC

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The synthesis of complex natural products from simple and common intermediates has been one of the major goals in synthetic organic chemistry. Toward this objective, if such simple scaffolds are suitably decorated with diverse functional groups they present opportunities not only to synthesize the target compounds but also construct the close analogues to investigate the biological properties. The Morita-Baylis-Hillman (MBH) reaction is an organocatalyzed CC bond forming reaction that leads to multifunctional products thereby offering viable alternatives for employing them for other complexity generating reactions. This property has been extensively utilized for the synthesis of natural products of microbial, animal, terrestrial, and marine origins. Simultaneously, MBH adducts are precursors to several drug molecules or their intermediates. This comprehensive review assimilates applications of the Morita-Baylis-Hillman reaction for the synthesis of different natural products and drug molecules.

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“…20 So, Baylis-Hillman adducts are of valuable synthetic intermediates for the synthesis of a number of complex molecules, biologically active molecules as well as natural products. [29][30][31][32][33][34][35][36][37][38] Recently, we have described applications of Baylis-Hillman adducts and many excellent results were also demonstrated. [39][40][41][42][43][44] As a continuation of our previous work, herein, we disclose a facile, regio-and stereoselective Baylis-Hillman acetates with various primary amines under the catalyst-and solvent-free conditions.…”

Section: -8mentioning

confidence: 99%