The Total Synthesis of Santonin

Abe, Yasuo; Harukawa, Tadatsugu; Ishikawa, Hisashi; Miki, Takuichi; Sumi, Masao; Toga, Tadashi

doi:10.2183/pjab1945.30.116

Cited by 12 publications

(1 citation statement)

References 5 publications

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“…[41] Commercially available by extraction, [42] this eudesmanolide provides a perfect starting point for the synthesis of various sesquiterpene lactones. Abe et al [43] and Marshall et al [44] also succeeded in its total synthesis starting from a hexahydronaphthalene derivative or 3-methylbenzoic acid, respectively. In the former approach, resolution of an advanced intermediate was possible to give access to enantiopure 125.…”

Section: Hemi-synthesis Starting From Santoninmentioning

confidence: 99%

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

Schall

Reiser

2008

Eur J Org Chem

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The biosynthetic pathways of sesquiterpene lactones are described in conjunction with recent developments in the total syntheses of various biologically active guaianolides. Different strategies towards the 5,7,5‐membered ring system are highlighted. Oxidative diol cleavages, aldol reactions, and intramolecular cyclopropanations were used as key reactions to construct the racemic guaianolide core system. Radical cyclizations, as well as ring closing metathesis, were successfully applied in asymmetric approaches. Biomimetic reactions were also applied as versatile tools for the construction of these highly complex natural products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Hemi-synthesis Starting From Santoninmentioning

confidence: 99%

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

Schall

Reiser

2008

Eur J Org Chem

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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The Michael condensation in its original scope is the addition of an addend or donor containing an alpha‐hydrogen atom in the system OCCH to a carbon‐carbon double bond that forms part of a conjugated system of the general formula CCCO in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta‐unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

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Gewinnung von 1;4‐Bisdehydro‐3‐oxo‐steroiden. Über Steroide, 139. Mitteilung

Meystre

Frey

Voser

et al. 1956

Helvetica Chimica Acta

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734 IIELVETICA CHIMICA ACTA. vorderlappens unterstutzt. Dasselbe wird je nach Bedarf vom Hypophysenvorderlappen geliefert. Es dringt in die Schilddrusenbl'dschen ein und aktiviert hier die Zellfermente soweit, dass einc genugende Versorgung des Korpers mit Schilddrusenhormon ernioglirht wird. Eine solche Verteilung der Regulation auf zwei verschiedene Organe (Schilddruse und Hypophysenvordcrlappen) ermoglicht einerseits eine Ablagerung, anderseits einen geregelten Verbrauch des gespeichwten Hormons. Z u s a m m c n f a s s u n g . h l s gimstigste Versuchsbedingungen h i m Studinm der Wirksamkeit der Schilddrusenkathepsine erwiesen sieh cine Temperatur von 40°, ein pH-Wert von 4,s his 4,8, d. h. ganz in der NLhe des isoclektrischen Punktes des Thyreoglobulins, und ein Busatz von 0,08 yo Cystein. Der in so zubereiteten Schilddr.iisenauszug~ii ablmfende Eiweissabbau wurde durch Bestimmung Cics Gesamtjod-und Gesamt-N-Gehaltes der einzelnen Eiweissfraktionen n'dher untersuclit . Der Proteinabbau durch die Eigenfermentc der Schilddrusenblaschen ist bei in. vitro-Versuchen zwar kraftig, jedoch schwiirher als beim Abbau durch die Pankreasfermente. n~edizinisch-chemisehex Institui der Universitat Bern.88. Gewinnung yon 1 ; 4-Bisdehydro-3-0x0-steroiden. fjber Steroide, 139. Mitteilungl) von Ch. Meystre, H. Frey, W. Voser und A. Wettstein. (9.11.56.)In vier friiheren M i t t e i l~n g e n~-~) haben wir uber die Herstellung von 1 j 4-Bisdehydro-3-0x0-steroiden aus d 4-3-0x0-steroiden auf mikrobiologischem Wege berichtet. Solche Umwandlungen, die u. a. zu hochaktiven Corticosteroiden6) fuhren, sind auch von anderer Seite beschrieben w~r d e n~)~)~" ) .

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The Total Synthesis of Santonin

Cited by 12 publications

References 5 publications

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Gewinnung von 1;4‐Bisdehydro‐3‐oxo‐steroiden. Über Steroide, 139. Mitteilung

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