A novel convergent approach to trans-fused polyether frameworks based on the reaction of vinylstannanes and triflates and its application to a synthetic study of the EFGH ring system of gambierol

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5769-5772

  Kadowaki, Chie ^a   Chan, Philip W H ^a   Kadota, Isao ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Coupling; Polycyclic ether; Triflate; Vinylstannane

Indexed keywords

GAMBIEROL; ORGANOTIN COMPOUND; POLYETHER DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; EPOXIDATION; PURIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034702516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00952-7     Document Type: Article

References (16)

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15. 6) 4.68 (d, J=5.3, 1H), 3.75 (m, 1H), 3.65, (dd, J=11.0, 4.4, 1H), 3.48 (ddd, J=9.5, 9.5, 1.7, 1H), 3.41 (ddd, J=11.2, 11.2, 2.8, 1H), 3.33-3.22 (m, 1H), 3.11 (ddd, J=11.4, 11.4, 2.1, 1H), 2.87 (d, J=14.4, 1H), 2.39 (d, J=15.9, 1H), 2.20 (dd, J=14.3, 9.6, 1H), 2.02 (dd, J=15.9, 5.7, 1H), 1.86-1.71 (m, 2H), 1.60-1.12 (m, 10H), 0.93 (s, 9H), 0.00 (d, J=2.7, 6H).
16. -) functional group, gave product 4d in 20% yield. In contrast, no reaction was observed for either the tosylate or mesylate versions of 2d. Reaction of 2d where the triflate was replaced by iodide furnished unknown decomposition products. Also, no coupling was observed for the in situ reaction of the vinyl iodide equivalent of 3b with 2d. Reaction of 3a with the aldehyde of 2d resulted in only enolization of the aldehyde.