Enantiopure building blocks for marine natural products via differentiation of enantiotopic groups

Beil, Winfried; Jones, Peter G.; Nerenz, F.; Winterfeldt, Ekkehard

doi:10.1016/s0040-4020(98)00158-6

Cited by 18 publications

(6 citation statements)

References 18 publications

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“…Based on the enantioselective cycloaddition of the optically pure cyclopentadiene (4) (226). Face selectivity was successfully achieved in the cycloaddition of cyclopentadiene 327 and spiroxazoline 328 to form the enantiopure 329.…”

Section: B Synthesis Of Spirocyclohexadienylisoxazolinementioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

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Section: B Synthesis Of Spirocyclohexadienylisoxazolinementioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

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“…For compounds that contain a spirohexadienone moiety in their structures, see: Wright & Kö nig (1993); Kö nig et al (1990); Beil et al (1998) and for their biological activities, see: Glushkov et al (2010); Pereira et al (2007). For strategies for the synthesis of spiro-hexadienones from Morita-Baylis-Hillman adducts, see: Coelho et al (2002); Ferreira et al (2009); Pirovani et al (2009); Martins et al (2014).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 3-methoxycarbonyl-2-(4-methoxyphenyl)-8-oxo-1-azaspiro[4.5]deca-1,6,9-trien-1-ium-1-olate

et al. 2014

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The title compound, C 18 H 17 NO 5 , was prepared by a synthetic strategy based on the Heck reaction from Morita-BaylisHillman adducts. The five-membered ring adopts a slightly twisted conformation on the C a -C m (a = aromatic and m = methylene) bond. The dihedral angle between the fivemembered ring and the spiro aromatic ring is 89.35 (7) ; that between the five-membered ring and the 4-methoxybenzene ring is 4.65 (7). Two short intramolecular C-HÁ Á ÁO contacts occur. In the crystal, molecules are linked by C-HÁ Á ÁO hydrogen bonds to generate a three-dimensional network.Keywords: single-crystal X-ray study; spirohexadienone structure; MoritaBaylis-Hillman aducts.CCDC reference: 1030399 Related literature Data collectionBruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS;Bruker, 2010)

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“…Based on the enantioselective cycloaddition of the optically pure cyclopentadiene (4) with spirolactone (224,225), Winterfeldt et al synthesized enantiomerically pure spiroxazoline 332, which is the crucial intermediate en route to the agelorins (87, 88) and their analogues (226). Face selectivity was successfully achieved in the cycloaddition of cyclopentadiene 327 and spiroxazoline 328 to form the enantiopure 329.…”

Section: B Synthesis Of Spirocyclohexadienylisoxazolinementioning

confidence: 99%

“…Flash-hydroxylation of 329 with ruthenium tetraoxide afforded cis-diol 329a, which underwent pyrolysis after it was transformed into the acetal 330 to generate the spirocyclohexenone 331. Subsequently, hydrolysis afforded the enantiopure intermediate 332, representing the agelorins (87, 88) chromophore (226).…”

Section: B Synthesis Of Spirocyclohexadienylisoxazolinementioning

confidence: 99%