Enantiospecific total synthesis of natural (-)-retigeranic acid A and two (-)-retigeranic acid B candidates

Paquette, Leo A.; Wright, Jonathan; Drtina, Gary J.; Roberts, R.A.

doi:10.1021/jo00389a070

Cited by 51 publications

(36 citation statements)

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“…In his synthesis of retigeranic acid (−)‐( 196 ) Paquette applied the Wittig–Still rearrangement in the construction of the strategic intermediate 204 , the “left half” of the target (the synthesis of the “right half” is not discussed here) . The synthesis began with the known aldehyde 197 , available in five steps from limonene (Scheme ).…”

Section: Applications To Total Synthesis Of Natural Productsmentioning

confidence: 99%

“…Paquette'ss ynthesis of retigeranica cid (À)-(196). [66] Angewandte Chemie Reviews sulfone 219 rearranged solely to the syn-220 isomer in 65 % yield (syn-and anti-r eferring to the orientation of the hydroxymethyl group and the thiopenylmethyl in 217 and the hydroxymethyl and phenylsulfonylmethyl moiety in 220). It is interesting that at least two equivalents of n-BuLi were necessary in the latter case.T he observed switch in the stereochemistry (and the need for two equivalents of base) was explained by the chelation of the lithium species generated by the abstraction of the more acidic a-proton of the sulfonyl group,asshown in TSG,Scheme 32.…”

Section: Terpenoidsmentioning

confidence: 99%

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Applications of the Wittig–Still Rearrangement in Organic Synthesis

Rýček

Hudlický

2017

Angew Chem Int Ed

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This Review traces the discovery of the Wittig-Still rearrangement and its applications in organic synthesis. Its relationship to Wittig rearrangements is discussed along with detailed analysis of E/Z- and diastereoselectivity. Modifications of the products arising from the Wittig-Still rearrangement are reviewed in the context of increased complexity in intermediates potentially useful in target-oriented synthesis. Early applications of the Wittig-Still rearrangement to modifications of steroids are reviewed as are applications to various terpene and alkaloid natural product targets and miscellaneous compounds. To the best of our knowledge, the literature is covered through December 2016.

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Section: Applications To Total Synthesis Of Natural Productsmentioning

confidence: 99%

Section: Terpenoidsmentioning

confidence: 99%

Applications of the Wittig–Still Rearrangement in Organic Synthesis

Rýček

Hudlický

2017

Angew Chem Int Ed

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“…In seiner Synthese von Retigeransäure (−)‐( 196 ) nutzte Paquette die Wittig‐Still‐Umlagerung zum Aufbau des strategischen Intermediats 204 , der “linken Hälfte” des Zielmoleküls (die Synthese der “rechten Hälfte” wird hier nicht diskutiert) . Die Synthese begann mit dem bekannten Aldehyd 197 , der in fünf Stufen aus Limonen erhältlich ist.…”

Section: Anwendungen In Der Totalsynthese Von Naturstoffenunclassified

Anwendungen der Wittig‐Still‐Umlagerung in der organischen Synthese

Rýček

Hudlický

2017

Angewandte Chemie

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Dieser Aufsatz zeichnet die Entstehung der Wittig‐Still‐Umlagerung und deren Anwendung in der organischen Synthese nach. Ihre Beziehung zur Wittig‐Umlagerung wird diskutiert, einhergehend mit einer detaillierten Analyse der E/Z‐Selektivität und Diastereoselektivität. Modifikationen der in Wittig‐Still‐Umlagerungen gebildeten Produkte werden im Zusammenhang der gesteigerten Komplexität von Intermediaten mit potenziellem Nutzen für die zielorientierte Synthese erläutert. Frühe Anwendungen der Wittig‐Still‐Umlagerung zur Modifizierung von Steroiden werden ebenso besprochen wie Anwendungen in der Naturstoffsynthesen von Alkaloiden und Terpenen sowie der Synthese sonstiger Verbindungen. Nach unserem besten Wissen ist die Literatur bis Dezember 2016 abgedeckt.

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“…From a biosynthetic point of view, its related sesterterpenoids include nitidasin, nitiol, and retigeranic acid A, (Figure ). Despite the pioneering syntheses of retigeranic acid A from Corey, Paquette,, Hudlicky,, and Wender group and the recent elegant synthesis of nitidasin from the Trauner group,– synthesis of astellatol has not been achieved . The highly congested pentacyclic skeleton that contains extremely rare 5‐7‐4‐6 fused ring system, ten stereocenters and three quaternary centers, makes astellatol arguably one of the most challenging targets for sesterterpenoid synthesis.…”

Section: Figurementioning

confidence: 99%