Synthesis of optically active trans-cyclononenes A possible approach to xenicanes

Liu, Gui; Smith, T. C.; Pfander, Hanspeter

doi:10.1016/0040-4039(95)00938-9

Cited by 18 publications

(13 citation statements)

References 15 publications

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“…As starting material we chose the Hajos − Parrish diketone 2 , which is readily available in enantiomerically pure form. Preliminary results have been disclosed previously as a short communication 1 Retrosynthetic Analysis …”

Section: Resultsmentioning

confidence: 97%

Total Synthesis of Coraxeniolide-A

2000

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The first total synthesis of optically active coraxeniolide-A (1a) and 4-epi-coraxeniolide-A (1b) is described. The approach is highly stereoselective and flexible in the preparation of a wide variety of members of the xeniolide family. The use of the Grob-fragmentation was pivotal for the stereospecific elaboration of the nine-membered ring. Coraxeniolide-A (1a) was synthesized in 28 steps by using the Hajos-Parrish diketone 2 as starting material which is available enantiomerically pure.

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Section: Resultsmentioning

confidence: 97%

Total Synthesis of Coraxeniolide-A

2000

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“…It took some 18 years from the first isolation of a xenicane family member in 1977 [22] until publication of the first synthetic studies on this compound class. Only in 1995, Pfander reported the first synthesis of a bicyclic xenicane ring system, which could potentially serve as a basis for the synthesis of a number of xenicane terpenoids [136]. Building on this initial work, Leumann and Pfander were indeed able to elaborate the total synthesis of coraxeniolide A in 2000 (Scheme 2) [58].…”

Section: Leumann and Pfander's Synthesis Of Coraxeniolide Amentioning

confidence: 99%

Xenicane Natural Products: Biological Activity and Total Synthesis

Betschart¹,

Altmann²

2015

CPD

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The xenicanes are a large class of mostly bicyclic marine diterpenoids featuring a cyclononane ring as a common structural denominator. After a brief introduction into the characteristic structural features of xenicanes and some biogenetic considerations, the major focus of this review will be on the various biological activities that have been reported for xenicanes and on efforts towards the total synthesis of these structures. Several xenicanes have been shown to be potent antiproliferative agents in vitro, but activities have also been reported in relation to inflammatory processes. However, so far, data on the possible in vivo activity of xenicanes are lacking. The major challenge in the total synthesis of xenicanes is the construction of the nine-membered ring. Different strategies have been pursued to establish this crucial substructure, including Grob fragmentation, ring-closing olefin metathesis, or Suzuki cross coupling as the enabling transformations.

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“…In 1995, Pfander reported the synthesis of an important building block [ 24 ] for the total synthesis of coraxeniolide A ( 10 ) [ 12 ], starting from chiral (−)-Hajos–Parrish diketone ( 58 ) [ 39 ]. Based on Pfander's seminal work, the first total synthesis of a xenicane diterpenoid was then accomplished by Leumann in 2000 ( Scheme 6 ) [ 40 ].…”

Section: Reviewmentioning

confidence: 99%

“…The total syntheses of coraxeniolide A ( 10 ) and β-caryophyllene ( 22 ) reported by Corey [ 46 ] in 2008 are based on Pfander’s idea [ 24 ] to construct the cyclononene fragment from (−)-Hajos–Parrish diketone ( 58 ) [ 39 ] ( Scheme 8 ). Chiral hydroxy dione 77 was synthesized according to a literature-known procedure [ 47 ].…”

Section: Reviewmentioning

confidence: 99%

“…For example, a class of bicyclic sesquiterpenes, caryophyllenes [ 21 ], exhibit the same bicyclo[7.2.0]undecane skeleton as xeniaphyllanes. Furthermore, while monocyclic azamilides [ 22 ] are seco-A-ring diterpenoids that are acylated with fatty acids, Dictyota diterpenes [ 23 – 24 ] either bear a similar seco-ring fragment, as observed for dictyodiol ( 24 ), or comprise a fused γ-butyrolactone moiety, as in dictyolactone ( 25 , Fig. 3 ).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

Huber¹,

Weisheit²,

Magauer³

2015

Beilstein J. Org. Chem.

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SummaryThis review describes strategies for the chemical synthesis of xenicane diterpenoids and structurally related metabolites. Selected members from the four different subclasses of the Xenia diterpenoid family, the xenicins, xeniolides, xeniaphyllanes and xeniaethers, are presented. The synthetic strategies are discussed with an emphasis on the individual key reactions for the construction of the uncommon nine-membered carbocycle which is the characteristic structural feature of these natural products. Additionally, the putative biosynthetic pathway of xenicanes is illustrated.

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Synthesis of optically active trans-cyclononenes A possible approach to xenicanes

Cited by 18 publications

References 15 publications

Total Synthesis of Coraxeniolide-A

Total Synthesis of Coraxeniolide-A

Xenicane Natural Products: Biological Activity and Total Synthesis

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

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