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Volumn 5, Issue 11, 2003, Pages 1923-1926

Synthesis of the [5-7-6] tricyclic core of guanacastepene a via an intramolecular Mukaiyama aldol reaction

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; GUANACASTEPENE A; UNCLASSIFIED DRUG; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GUANACASTEPENE;

EID: 0042853256     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0344873     Document Type: Article
Times cited : (32)

References (36)
  • 1
    • 0026760182 scopus 로고
    • Neu, H. C. Science 1992, 257, 1064.
    • (1992) Science , vol.257 , pp. 1064
    • Neu, H.C.1
  • 22
    • 0141825104 scopus 로고    scopus 로고
    • note
    • Similar to Hanna's approach (ref 3q) to construct seven- and six-membered rings simultaneously through ring-closing metathesis, our initial strategy was to generate the seven- and six-membered ring of guanacastepene A at the same time as shown below: (equation presented) Starting from the (E)-vinyl iodide known in the literature, the skeletal framework of guanacastepene A was assembled rapidly in four steps. However, the intramolecular Diels-Alder reaction (IMDA) to generate the [5-7-6] core structure of guanacastepene A did not take place even with various modifications on either the diene or the dienophile moiety. Nonetheless, the design of our current synthetic plan benefited greatly from our initial approach because the same reaction tools such as organocuprate coupling, Diels-Alder reaction, and tandem conjugate addition/aldol reaction are maintained.
  • 36
    • 0141602009 scopus 로고    scopus 로고
    • note
    • 4 in the Mukaiyama aldol reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.