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Volumn 49, Issue 37, 2010, Pages 6673-6675

Asymmetric total synthesis of solandelactone E: Stereocontrolled synthesis of the 2-ene-1,4-diol core through a lithiation-borylation-allylation sequence

Author keywords

1,4 ene diols; Allyl silanes; Lithiation borylation; Natural products; Total synthesis

Indexed keywords

1,4-ENE-DIOLS; ALLYL SILANES; LITHIATION; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 77956510772     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003236     Document Type: Article
Times cited : (46)

References (43)
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    • for a review on carbonyl allylborations, see
    • for a review on carbonyl allylborations, see:
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    • Taber used nBuLi as the base but we found that NaHMDS gave higher yields
    • D. F. Taber, G. Bui, B. Chen, J. Org. Chem. 2001, 66, 3423-3426. Taber used nBuLi as the base but we found that NaHMDS gave higher yields.
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    • Taber, D.F.1    Bui, G.2    Chen, B.3
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    • Problems with this strategy in the construction of eightmembered lactones have been encountered before, see references 5 and 6
    • Problems with this strategy in the construction of eightmembered lactones have been encountered before, see references [5] and [6].
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    • Nucleophilic additions to related trans cyclopropanes usually occur without stereoinduction, see reference 9. In our case, the very high stereochemical control observed is dominated by the stereochemistry of the allylborating agent and by the influence of the 9-BBN moiety. 9-BBN = 9-borabicyclo3.3.1nonane
    • Nucleophilic additions to related trans cyclopropanes usually occur without stereoinduction, see reference [9]. In our case, the very high stereochemical control observed is dominated by the stereochemistry of the allylborating agent and by the influence of the 9-BBN moiety. 9-BBN = 9-borabicyclo[3.3.1]nonane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.