Total synthesis and structural revision of vannusals A and B: synthesis of the true structures of vannusals A and B.
Total synthesis and structural revision of vannusals A and B: synthesis of the true structures of vannusals A and B.
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DOI：
10.1021/ja100742b
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发表时间：
2010-05-26
影响因子：
15
通讯作者：
Guella, Graziano
中科院分区：
文献类型：
--
作者：
Nicolaou, K. C.;Ortiz, Adrian;Zhang, Hongjun;Guella, Graziano
Having determined, through total synthesis, that the originally assigned structure of vannusals A and B were incorrect, we set out to uncover the identity of the true structures of these novel marine natural products. Our search was based on intelligence gathered by NMR spectroscopy and chemical synthesis and took us through the total synthesis of eight diastereomeric vannusal B structures [2, d-2, 3, d-3, 4, d-4, 5, and d-5, Figure 1]. The true structures of vannusals A and B were finally determined to be d-5 and d-1, respectively. Their total synthesis was based on a highly convergent and efficient strategy that involved fragments vinyl iodide (−)-6 and aldehyde (±)-94, and featured a stereoselective lithium-mediated coupling reaction and a samarium-induced cyclization process that forged the final ring of the carbon framework. The synthetic strategies and technologies developed in these investigations expand the scope of chemical synthesis and render these compounds readily available for biological evaluation, while the NMR spectroscopic insights gained should prove useful in future structural determination endeavors.
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影响因子：
16.6
作者：
Nicolaou, K. C.;Zhang, Hongjun;Dagneau, Philippe
通讯作者：
Dagneau, Philippe
影响因子：
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Smith, Steven G.;Paton, Robert S.;Goodman, Jonathan M.
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Burton, Jonathan W.
影响因子：
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NISHIZAWA, M
影响因子：
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通讯作者：
MARTIN, JC