Total Synthesis of Natural (+)-Acetoxycrenulide

Paquette, Leo A.; Wang, Tingzhong; Pinard, Emmanuel

doi:10.1021/ja00109a041

Cited by 39 publications

(12 citation statements)

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“…We envisioned a more efficient route using a highly enantiomerically enriched citronellol (Hanessian et al, 1990;Ho, 1992 eton is commonly used in the synthesis of natural products (e.g., Mori et al, 1991;Stork and Nakamura, 1983;Ho, 1992;Mori and Harashima, 1993a,b;Weinges et al, 1993;Mori and Murata, 1994;Paquette et al, 1995). Modifications at both termini of the citronellane skeleton can be performed without perturbing the chiral center (Ho, 1992).…”

Section: Discussionmentioning

confidence: 99%

Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

et al. 1995

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Abstract-Male coconut rhinoceros beetles, Orycres rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl 4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pherornone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps sjgnificantly enhanced attraction. With increasing dose, captures of O. rhinocerós'increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.

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Section: Discussionmentioning

confidence: 99%

Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

et al. 1995

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“…Paquette and co-workers disclosed the enantioselective total synthesis of the Xenia diterpenoid related crenulatane (+)-acetoxycrenulide ( 151 ) [ 65 – 67 ]. The skeleton of crenulatanes, which features an eight-membered carbocyclic ring fused to a cyclopropane ring, may be the product of a photoisomerization of xenicanes.…”

Section: Reviewmentioning

confidence: 99%

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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“…Asymmetric Michael additions using phosphonamides 28c , f , or analogs of 28 and 40 , respectively, were applied in the total synthesis of acetoxycrenulide ( 10 ) [ 41 – 42 ], berkelic acid ( 15 ) [ 43 ], estrone ( 12 ) [ 44 ], fumonisin B 2 ( 20 ) [ 45 – 47 ], methyl jasmonate ( 11 ) [ 48 ], and nudifloside A and D ( 13 ) [ 49 ], as discussed later in this review. Studies for the synthesis of the polyphenolic natural products tatanans A–C also explored the use of phosphonamide technology [ 50 ].…”

Section: Reviewmentioning

confidence: 99%

“…Paquette and co-workers reported the first and only total synthesis of this diterpene ( Fig. 4 ) [ 41 – 42 ]. The cyclooctanoid core of the target was envisioned to be formed by a Claisen rearrangement of intermediate 81 .…”

Section: Reviewmentioning

confidence: 99%

“…Face-selective Simmons–Smith cyclopropanation, reduction of both carbonyl groups, and chemoselective oxidation of the formed lactol with Fetizon’s reagent afforded 94 . The final steps of the synthesis involved conversion to the corresponding α,β-unsaturated lactone 95 and modification of the side chain to re-build the original double bond to eventually give (+)-acetoxycrenulide ( 10 ) [ 41 – 42 ].…”

Section: Reviewmentioning

confidence: 99%

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Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

Focken¹,

Hanessian²

2014

Beilstein J. Org. Chem.

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SummaryA review of the synthesis of natural products and bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be summarized, as well as an overview of the synthesis of the employed phosphonamide reagents.

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Total Synthesis of Natural (+)-Acetoxycrenulide

Cited by 39 publications

References 0 publications

Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

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