The Remaining Stereoisomers of the Sparteine Group

Carmack, Marvin; Douglas, Bryce; Martin, Eric W.; Suss, Hanna

doi:10.1021/ja01621a089

Cited by 19 publications

(9 citation statements)

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“…A practical stereocontrolled entry to all six stereoisomers of the characteristic sparteine skeleton is a desirable goal and would extend the versatility of existing asymmetric methods which rely on these intriguing compounds. Numerous racemic syntheses of the sparteine bases have appeared, − but few of these approaches are efficient and no obvious methods exist to render enantioselective the routes which are genuinely practical. Notwithstanding the plethora of known racemic routes to 1 − 3 , two enantioselective syntheses of sparteine itself have now been reported .…”

mentioning

confidence: 99%

A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core

et al. 2005

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[reaction: see text] The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to alpha-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography.

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mentioning

confidence: 99%

A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core

et al. 2005

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“…Lupinus pusillus ,211a, 220 Lupinus sericeus (silky lupine),221 Lupinus argenteus stenophyllus (silvery lupine), Lupinus solosericeus , Sophora secundiflora (Texas mountain laurel)…”

Section: Alkaloidsmentioning

confidence: 99%

Enantiomeric Natural Products: Occurrence and Biogenesis

et al. 2012

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In Nature, chiral natural products are usually produced in optically pure form; however, on occasion Nature is known to produce enantiomerically opposite metabolites. These enantiomeric natural products can arise in Nature from a single species, or from different genera and/or species. Extensive research has been carried out over the years in an attempt to understand the biogenesis of naturally occurring enantiomers, however, many fascinating puzzles and stereochemical anomalies still remain.

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“…Lupinus pusillus ,211a, 220 Lupinus sericeus (Seidenlupine),221 Lupinus argenteus stenophyllus (Silberlupine), Lupinus solosericeus , Sophora secundiflora (Meskalbohne)…”

Section: Alkaloideunclassified

“…Die Biosynthese aller Benzylisochinolinalkaloide geht vom L ‐Tyrosin aus und verläuft nach dem grundlegenden Benzylisochinolin‐Stoffwechselweg 232. 233 Wie in Schema dargestellt, ist die erste beteiligte Reaktion der BIA‐Synthese die asymmetrische Pictet‐Spengler‐Kondensation von Dopamin (aus Tyrosin) und p ‐Hydroxyphenylacetaldehyd (4‐HPAA) zu enantiomerenreinem ( S )‐Norcoclaurin, katalysiert von der Norcoclaurinsynthase (NCS) 221. In vier enzymatischen Stufen wird ( S )‐Norcoclaurin in enantiomerenreines ( S )‐Reticulin umgewandelt.…”

Section: Alkaloideunclassified

Enantiomere Naturstoffe: Vorkommen und Biogenese

et al. 2012

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In der Natur werden chirale Substanzen meist in enantiomerenreiner Form synthetisiert – manchmal entstehen aber auch beide Enantiomere. Solche enantiomeren Naturstoffe können von einer Art oder von verschiedenen Gattungen und/oder Arten gebildet werden. Intensive Forschungen wurden über viele Jahre durchgeführt, um die Biogenese natürlich vorkommender Enantiomere zu verstehen, doch viele faszinierende Rätsel und stereochemische Anomalien sind nach wie vor ungelöst.

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The Remaining Stereoisomers of the Sparteine Group

Cited by 19 publications

References 0 publications

A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core

A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core

Enantiomeric Natural Products: Occurrence and Biogenesis

Enantiomere Naturstoffe: Vorkommen und Biogenese

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