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Volumn 71, Issue 18, 2006, Pages 6892-6897

Synthetic study of 1,3-butadiene-based IMDA approach to construct a [5-7-6] tricyclic core and its application to the total synthesis of C8-epi-guanacastepene O

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; ESTERS; MOLECULAR DYNAMICS; SYNTHESIS (CHEMICAL);

EID: 33750483918     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060996h     Document Type: Article
Times cited : (43)

References (50)
  • 1
    • 0026760182 scopus 로고
    • Neu, H. C. Science 1992, 257, 1064.
    • (1992) Science , vol.257 , pp. 1064
    • Neu, H.C.1
  • 33
    • 33750468043 scopus 로고    scopus 로고
    • It is of note that Kwon and MacMillan groups revealed their efforts to generate the [5-7-6] core by an IMDA reaction (see refs 5m and http://etd.caltech.edu/etd/available/etd-10282003-135857/).
  • 34
    • 33750484060 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 49
    • 33750484745 scopus 로고    scopus 로고
    • note
    • Reduction of keto ester 35 proceeded with a good selectivity, and we believed the molecular conformation of 35 might play a major role in this outcome. Compound 35 shows a certain type of ball-shape, especially the axial methyl group at C8. which will guide the reducing agent to approach the C5 ketone from its top face at -95 °C (see its crystal structure of compound 35 listed below), leading to the formation of the desired stereochemistry at C5. The stereochemistry for the trans-relationship between the proton (a) at C5 and the protons (b) of the methyl group at C8 was confirmed by ID NOESY study of compound 36 (see Supporting Information for details).


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