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Volumn 21, Issue 49, 2015, Pages 17605-17609

Construction of Bridged Polycyclic Systems by Polyene Cyclization

Author keywords

bioinspired synthesis; bridged polycycles; cyclization; Lewis acids; meroterpenoids

Indexed keywords

BYPRODUCTS; CARBON; EMBEDDED SYSTEMS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 84948459814     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201503969     Document Type: Article
Times cited : (12)

References (116)
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    • Polyprenylated acylphloroglucinols (PPAPs) constitute a well-known family of meroterpenoids containing a bridged [3.3.1] bicyclic system, which is also biosynthesized through a dearomatization-cyclization sequence. For bioinspired total syntheses of PPAPs, see:
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    • The cedrene/funebrene and kaurane carbon frameworks were constructed, albeit in low yield, by a tandem reaction, wherein cationic polycyclization was combined with a hydride shift and pinacol rearrangement, respectively
    • The cedrene/funebrene and kaurane carbon frameworks were constructed, albeit in low yield, by a tandem reaction, wherein cationic polycyclization was combined with a hydride shift and pinacol rearrangement, respectively;
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    • Corey and Myers groups reported that 5-exo cyclizations occurred exclusively to afford [6,6,5,5]-fused tetracyclic compounds in the system capable of either 5-exo or 6-endo closure;
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    • See the Supporting Information for the preparation of substrates 1 d - h.
    • See the Supporting Information for the preparation of substrates 1 d-h.
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    • 3 complexes could induce cyclization through an intramolecular mode of action. See reference[7k].
    • 3 complexes could induce cyclization through an intramolecular mode of action. See reference[7k].
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    • Shenvi and Pronin suggested that a chloride anion could be generated by dissociation of either Lewis acid or its metallate anion, and aluminum Lewis acids are superior because the anions are most effectively sequestered away from the cation. See reference[9a].
    • Shenvi and Pronin suggested that a chloride anion could be generated by dissociation of either Lewis acid or its metallate anion, and aluminum Lewis acids are superior because the anions are most effectively sequestered away from the cation. See reference[9a].
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    • 2 at -78 C. This result clearly revealed the generation of the corresponding cation intermediate from 16 a, which did not react with the allylsilane moiety.
    • 2 at -78 C. This result clearly revealed the generation of the corresponding cation intermediate from 16 a, which did not react with the allylsilane moiety.
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    • 2 instead of TfOH resulted in complete recovery of 16 a.
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    • 2, 7]tridecane derivatives could be obtained by a 5-exo cyclization followed by rearrangement (i.e. 4′ → 2 in Scheme1); however, it is unlikely that the 5-exo cyclization proceeds to form an unstabilized cation intermediate like 4′.
    • 2, 7]tridecane derivatives could be obtained by a 5-exo cyclization followed by rearrangement (i.e. 4′ → 2 in Scheme1); however, it is unlikely that the 5-exo cyclization proceeds to form an unstabilized cation intermediate like 4′.
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    • [34] instead of bromide 9.
    • [34] instead of bromide 9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.