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Volumn 47, Issue 7, 1991, Pages 1215-1230

Enzymatic hydrolysis of cyclopropanes. Total synthesis of optically pure dictyopterenes a and c'.

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; PHEROMONE;

EID: 0026021948     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)86378-X     Document Type: Article
Times cited : (71)

References (29)
  • 3
    • 0000561788 scopus 로고
    • The cyclopropyl lactone (–)-(1S,2R)-cis-3-oxabicyclo(3,1,0)hexan-2-one was obtained in optically pure form by HLADH catalyzed oxidation of cis-1,2-bis(hydroxymethyl) cyclopropane., However this method requires an expensive NAD-coenzyme recycling system (approximative reagent cost: HLADH / NAD+ / FMN 60$ / 10 mmol of substrate). A cyclopropane compound of reported high optical purity was also obtained using the cheaper enzyme PLE (3$ / 10 mmol of substrate). PLE catalyzed hydrolysis of dimethyl cis-cyclopropane-1,2-dicarboxylate yielded the corresponding monoester with reported 94% ee and even 97% ee.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4659
    • Jakovac1    Goodbrand2    Lok3    Jones4
  • 5
    • 33845283189 scopus 로고
    • 3) for a reported 97% ee (determined after a 2 step derivatization). Moreover opposite absolute configurations are reported for the same acid ester.
    • (1987) J. Org. Chem. , vol.52 , pp. 4565
    • Sabbioni1    Jones2
  • 15
    • 0343952390 scopus 로고
    • Synthesis of (�)-Desmarestene and (�)-Viridiene, the Two Sperm Releasing and Attracting Pheromones from the Brown AlgaeDesmarestia aculeata andDesmarestia viridis
    • (1982) Helvetica Chimica Acta , vol.65 , pp. 2355
    • ]Boland1    Jakoby2    Jaenicke3
  • 16
  • 18
    • 0021886539 scopus 로고
    • The ee values reported by these authors have to be taken with precaution since their Dictyopterene A was contaminated with 10% of a Z stereoisomer (16a, note 17) and since the (+)-Dictyopterene C' ee refered to the natural product (–)-Dictyopterene C' which is known to have a 75% optical purity.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2779
    • Colobert1    Genet2
  • 20
    • 84918197461 scopus 로고    scopus 로고
    • Pale, P.; Grandjean, D.; Chuche, J., Tetrahedron Lett. to be submitted for publication.
  • 24
    • 84985129787 scopus 로고
    • Reaktionen mit Phosphinalkylenen; XXXII1. Herstellung und Reaktionen von Alkylidenphosphoranen (Phosphinalkylenen) in Hexamethylphosphorsäuretriamid unter Verwendung von OP[N(CH3)2]2 -und N(CH3)2 ⊖als Basen
    • (1974) Synthesis , pp. 798
    • Bestman1    Stransky2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.