A total synthesis of the aglycone of IB-00208 was accomplished in 22 steps using a newly developed approach towards polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones. The generality of this entry to xanthones was initially established on several model systems before it was successfully applied to the construction of the hexacyclic core of the natural product. A new and potentially general approach towards angularly-fused benzocyclobutenones using ring-closing metathesis (RCM) was also developed.

2015-01-02·Organic Letters1区 · 化学

Approaches to Polycyclic 1,4-Dioxygenated Xanthones. Application to Total Synthesis of the Aglycone of IB-00208

1区 · 化学

Article

作者: Yang, Jingyue ; Cheng, Bo ; Knueppel, Daniel ; Martin, Stephen F. ; Mans, Douglas

Hexacyclic xanthone natural products such as IB-00208 present a formidable challenge in organic synthesis. A new approach to polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones has been developed and applied to the first total synthesis of the aglycone of IB-00208. The 22-step synthesis features an acetylide stitching process that joins an aryl aldehyde with an angularly fused benzocyclobutenone, which was prepared by a ring-closing metathesis reaction. The resulting acetylenic benzocyclobutenone diol underwent a Moore rearrangement to give an intermediate that was further elaborated to the aglycone of IB-00208 as a mixture of hydroquinone-quinone tautomers.

2008-09-25·Journal of Medicinal Chemistry1区 · 医学

Synthesis and Antitumor Activity of Mechercharmycin A Analogues

1区 · 医学

Article

作者: Aligué, Rosa ; Hernández, Delia ; Cuevas, Carmen ; Álvarez, Mercedes ; Albericio, Fernando ; Altuna, Marta

Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.

100 项与 IB-06202 相关的药物交易

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