Novel Total Synthesis of (+)-Eremantholide A

Takao, Ken Ichi; Ochiai, Hiroshi; Yoshida, Ken; Hashizuka, Takahiko; Koshimura, Hirokazu; Tadano, Kin Ichi; Ogawa, S.

doi:10.1021/jo00130a017

Cited by 67 publications

(14 citation statements)

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“…[119,120] Total syntheses of 173 have been completed, notably by the groups of Hale, [121] Boeckman, [122] and Tadano. [123] Given that 172 is close in structure to atripliciolide tiglate (174), which was reported by Bohlmann et al (Figure 31), [124] and to many other family members in this series, [125] Le Quesne and Raffauf suggested that a close relationship must exist between the genera Eremanthus, Lychnophora, Piptolepis, and Vanillosmopsis in the family Vemoniae. [119] 4.6.…”

Section: -Oxabicyclo[621] Systemssupporting

confidence: 64%

Natural Products with Anti‐Bredt and Bridgehead Double Bonds

2014

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Well over a hundred years ago, Professor Julius Bredt embarked on a career pursuing and critiquing bridged bicyclic systems that contained ring strain induced by the presence of a bridgehead olefin. These endeavors founded what we now know as Bredt's rule (Bredtsche Regel). Physical, theoretical, and synthetic organic chemists have intensely studied this premise, pushing the boundaries of such systems to arrive at a better understood physical phenomenon. Mother nature has also seen fit to construct molecules containing bridgehead double bonds that encompass Bredt's rule. For the first time, this topic is reviewed in a natural product context.

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Section: -Oxabicyclo[621] Systemssupporting

confidence: 64%

Natural Products with Anti‐Bredt and Bridgehead Double Bonds

2014

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“…171 erwies sich als stark cytotoxisch, mit über zehnmal höheren Werten als das verwandte Eremantholid A ( 173 ; Abbildung 31). 119, 120 Vollständige Totalsynthesen von 173 führten die Gruppen um Hale,121 Boeckman122 und Tadano durch 123. Da 172 strukturell sehr dem von Bohlmann et al.…”

Section: Sauerstoff‐haltige Bicyclische Brückenkopf‐alkeneunclassified

Naturstoffe mit Anti‐Bredt‐ und Brückenkopf‐Doppelbindung

2014

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Vor über hundert Jahren begann Professor Julius Bredt seine Forschungskarriere auf dem Gebiet der verbrückten bicyclischen Systeme, die durch ein Brückenkopf‐Alken unter Ringspannung stehen. Seine kritischen Betrachtungen mündeten in der Formulierung dessen, was wir heute als die Bredtsche Regel kennen. Seitdem versuchen Physikochemiker, Theoretiker und Synthesechemiker gleichermaßen, die Grenzen dieses physikalische Phänomens auszuloten, um es besser kennenzulernen. Der Bauplan der Natur sieht durchaus Brückenkopf‐Doppelbindungen nach der Bredtschen Regel vor. In diesem Aufsatz wird erstmals die Anwendung der Bredtschen Regel auf Naturstoffe umfassend erörtert.

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“…[1][2][3][4][5] The biological activity of some eremantholides, which includes trypanocidal, 6 antibacterial, 7 anti-inflammatory 8,9 and anti-tumor properties, 10 has prompted several research groups to propose syntheses, both total and partial, for these compounds. [11][12][13][14][15][16][17][18] Nevertheless, most efforts in these synthetic works are directed toward the obtention of eremantholide A (1) and just a few were undertaken toward other eremantholide structures or some generic part of eremantholides structures.…”

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confidence: 99%