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Volumn 49, Issue 6, 2010, Pages 1103-1106

Catalytic asymmetric total synthesis of ent-hyperforin

Author keywords

Asymmetric synthesis; Claisen rearrangement; Homogeneous catalysis; Natural products; Rearrangement

Indexed keywords

ASYMMETRIC SYNTHESIS; ASYMMETRIC TOTAL SYNTHESIS; CLAISEN REARRANGEMENT; DIASTEREOSELECTIVE; DIELS-ALDER REACTION; HOMOGENEOUS CATALYSIS; HYPERFORINS; INTRAMOLECULAR ALDOL REACTIONS; IRON CATALYST; NATURAL PRODUCTS; PUMMERER REARRANGEMENTS;

EID: 76249122299     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906678     Document Type: Article
Times cited : (128)

References (45)
  • 10
  • 26
    • 76249110269 scopus 로고    scopus 로고
    • In this study, chiral ligand 6 derived from inexpensive (R)-4hydroxyphenylglycine was used in the catalytic asymmetric Diels-Alder reaction between 7 and 8, thus resulting in the synthesis of the antipode of natural 1.
    • In this study, chiral ligand 6 derived from inexpensive (R)-4hydroxyphenylglycine was used in the catalytic asymmetric Diels-Alder reaction between 7 and 8, thus resulting in the synthesis of the antipode of natural 1.
  • 28
    • 76249108935 scopus 로고    scopus 로고
    • During the scale-up studies, it was found that the enantioselectivity of this catalytic Diels-Alder reaction was improved to up to 96% ee (87% ee in Ref. [11]) by using strict temperature control and moisture exclusion.
    • During the scale-up studies, it was found that the enantioselectivity of this catalytic Diels-Alder reaction was improved to up to 96% ee (87% ee in Ref. [11]) by using strict temperature control and moisture exclusion.
  • 29
    • 76249101952 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • a) See the Supporting Information for details;
  • 30
    • 76249106718 scopus 로고    scopus 로고
    • when, the catalytic asymmetric Diels-Alder reaction was conducted on greater than 10 g scales, a decline in the ee value was observed, probably because of the slight increase in the reaction temperature during the addition of substrates.
    • b) when, the catalytic asymmetric Diels-Alder reaction was conducted on greater than 10 g scales, a decline in the ee value was observed, probably because of the slight increase in the reaction temperature during the addition of substrates.
  • 34
    • 76249123852 scopus 로고    scopus 로고
    • The hydrolysis of the enol TIPS ether provided a 1:1 mixture of C1 isomers. Although further conversion was described from one isomer (14) in the text, the other isomer was also utilized for the synthesis of intermediate 10 with comparable efficiency; see the Supporting Information for details.
    • The hydrolysis of the enol TIPS ether provided a 1:1 mixture of C1 isomers. Although further conversion was described from one isomer (14) in the text, the other isomer was also utilized for the synthesis of intermediate 10 with comparable efficiency; see the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.