Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Musich, James A.; Rapoport, Henry

doi:10.1021/ja00483a037

Cited by 71 publications

(21 citation statements)

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“…Among the better known examples of carnitinerelated naturally-occurring compounds are: a new carnitine transport carrier isolated from human testis [Enomoto et al, 2002] and a carnitinoid structure embedded in anthopleurine, the natural alarm pheromone isolated from Anthopleura elegantissima [Musich and Rapoport, 1978].…”

Section: Mitochondrial Targeting Systemsmentioning

confidence: 99%

Lactic acid in cancer and mitochondrial disease

Steliou

Perrine

Faller

2009

Drug Development Research

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Cancer and the mitochondrial diseases are disparate disorders that have in common a failure of normal cellular respiratory activity in disease-affected tissues. In mitochondrial diseases, the impairment in the mitochondria is often the result of abnormalities in their mtDNA, whereas in cancerous cells, the altered respiration is driven by the Warburg effect. The oxidation of glucose (as pyruvate in the mitochondria) is inhibited and energy production relies on cytoplasmic glycolysis. This suppressed mitochondrial activity confers in tumor cells a state of resistance to apoptosis and, in mitochondrial diseases like mitochondrial encephalopathy, lactic acidosis, and stroke-like episodes (MELAS), the altered respiration leads to lactic acidosis. Driving glucose to its complete oxidation inside the mitochondria has potential in cancer therapy to reconstitute apoptotic competence in tumor cells and, in mitochondrial disease, to treat lactic acidosis. This minireview investigates the development of small molecule agents for suppressing the Warburg effect in cancer therapy and lactic acidosis in mitochondrial disease. Drug Dev Res 70 : 499-511, 2009.

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Section: Mitochondrial Targeting Systemsmentioning

confidence: 99%

Lactic acid in cancer and mitochondrial disease

Steliou

Perrine

Faller

2009

Drug Development Research

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“…A soln. of 6 [22] in THF (50 ml) was added to a soln. of PhMgBr (from Mg (8.8 g, 0.36 mol) and PhBr (37.8 ml, 0.36 mol)) in THF (340 ml) over 1 h. The temp.…”

Section: Experimental Partmentioning

confidence: 99%

“…Reaction of 6 [22] with excess phenyl Grignard reagent (+7a), esterification (+7b), NaBH, reduction (+Sa), substitution of the primary OH group by C1 with CCl,/PPh, (+8b), ether formation (+ 8c), and replacement of C1 by PPh, gave the MeO-substituted phosphane 9 in an overall yield of ca. 40%.…”

mentioning

confidence: 99%

Preparation of the PdCl₂ Complex of TADDOP, the Bis(diphenylphosphinite) of TADDOL: Use in enantioselective 1,3‐diphenylallylations of nucleophiles and discussion of the mechanism

Seebàch¹,

Devaquet

Ernst

et al. 1995

Helvetica Chimica Acta

105

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Reaction of the tartrate-derived diol (R,R)-d, CI, a',a'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (TADDOL) with chlorodiphenylphosphane gives a new bis(diphenylphosphany1) ligand (TADDOP). The complex 4 formed with PdCI, has been crystallized and its structure determined by X-ray diffraction (Fig. I). The complex is used for Pd-catalyzed enantioselective 1,3-diphenylaIlylations of various nucleophiles which give products with enantiomer ratios of up to 88 : 12 (Scheme 2). Crystallization procedures lead to the enantiomerically pure ( > 99 : 1) product 11 derived from dimethyl malonate. The structure of the TADDOP complex 4 is compared with those of other transition-metal complexes containing chelating bis(diphenylphosphany1) ligands (Fig. 2). A crystallographic data base search reveals that the structures of transition-metal complexes containing two Ph2P groups (superpositions in Fzg.3) fall into one of two categories: one with approximate C, symmetry and the other with C s mmetry (20 and 19 examples, resp.). A mechanistic model is proposed which correlates the conformational chirality (6 or A ) of the four Ph groups' arrangement in such complexes with the topicity of nucleophile approach on Pd-bound trans,trans-l,3-diphenylallyl groups (Scheme 3 and Table).

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“…(R,R)-Tartaric acid was converted to a mixture of diasteriomeric stegobinones (1161) (483), confirming the indicated 2R,3R configuration of the natural drugstore beetle pheromone. This same starting material also led to anthopleurine (1162) (484), a sea anenome alarm pheromone. A structurally unique pheromone (485) of a dermestid beetle is the dihydrofuran 1170 (Scheme 87).…”

Section: E Insect Pheromones and Related Compoundsmentioning

confidence: 88%

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

Scott

1984

Asymmetric Synthesis

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Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Abstract: Acknowledgment. Support for this research was generously provided by the National Institutes of Health (Grant CA-16616), Chevron Research Co., and Eli Lilly Co., as well as (through department Equipment Grant CHE-76-05512) the National Science Foundation.

Cited by 71 publications

References 5 publications

Lactic acid in cancer and mitochondrial disease

Lactic acid in cancer and mitochondrial disease

Preparation of the PdCl₂ Complex of TADDOP, the Bis(diphenylphosphinite) of TADDOL: Use in enantioselective 1,3‐diphenylallylations of nucleophiles and discussion of the mechanism

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

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Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Abstract: Acknowledgment. Support for this research was generously provided by the National Institutes of Health (Grant CA-16616), Chevron Research Co., and Eli Lilly Co., as well as (through department Equipment Grant CHE-76-05512) the National Science Foundation.

Cited by 71 publications

References 5 publications

Lactic acid in cancer and mitochondrial disease

Lactic acid in cancer and mitochondrial disease

Preparation of the PdCl2 Complex of TADDOP, the Bis(diphenylphosphinite) of TADDOL: Use in enantioselective 1,3‐diphenylallylations of nucleophiles and discussion of the mechanism

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

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Preparation of the PdCl₂ Complex of TADDOP, the Bis(diphenylphosphinite) of TADDOL: Use in enantioselective 1,3‐diphenylallylations of nucleophiles and discussion of the mechanism