Tetrahedron

The synthesis of 3-hydroxymethylfuro [3, 2-b] naphtho [2, 3-d] furan-5, 10-dione, a novel metabolite isolated from Crescentia cujete

LB Nielsen, R Slamet, D Wege

文献索引：Nielsen, Linda B.; Slamet, Riskiono; Wege, Dieter Tetrahedron, 2009 , vol. 65, # 23 p. 4569 - 4577

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被引用次数: 7

摘要

The title natural product 1, which possesses a new ring skeleton, has been synthesised by a sequence in which the key steps involve a tandem intramolecular Diels–Alder/reverse Diels– Alder reaction sequence. Thus 3-(2-furyl)-1, 4-dimethoxynaphthalen-2-ol was treated with ethyl 3-bromopropiolate, and without isolation, the resulting acetylenic ether was heated in the presence of 3, 6-di (pyridin-2-yl)-1, 2, 4, 5-tetrazine. Intramolecular addition of the ...