P-82 プロロセンチンの全合成研究(ポスター発表の部)
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概要
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Prorocentin, isolated from dinoflagellate Prorocentrum lima by Lu et al., exhibits inhibitory activity against some human cancer cell lines [IC_<50>: 16.7μg/mL (DLD-1); 83.6μg/mL (RPMI7951)] and possesses an unique polyether structure, featured by a [6,6]-spirocyclic acetal fused with an oxane ring (BCD-ring), an epoxide (A-ring), a five membered ether (E-ring), and a side chain including a conjugated triene group. Although the absolute configuration of prorocentin has not yet been determined, its biological and structural features make it an attractive synthetic target. Thus, a project toward the total synthesis of prorocentin aiming at determination of the absolute stereochemistry has been commenced. The partial relative stereochemistry of prorocentin was proposed by Lu et al. from their intensive NMR experiments, and a possible stereostructure was also shown as 1 in their report. Therefore, we first elucidated a synthetic plan for prorocentin based on the stereochemistry of 1. At the final stage in the synthesis, assembly of 1 from dienyl boran 2 and iodoalkene 3 via a Suzuki-Miyaura coupling followed by removal of TBS group and the simultaneous epoxide formation is intended. Iodoalkene 3 would be derived from C8-C35 segment 4 in a few steps including Takai olefination and protective group manipulation. So far, we have synthesized segments 2 and 4, and examined the above transformation processes (4→3 and 3+2→1) in a model system. Details of the synthesis of 4, based on 6-endo Utimoto cyclization to create the B-ring and intramolecular double conjugate addition to produce the CD-ring, and the model experiments will be described in the poster session.
- 2008-09-01
著者
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竹村 淳志
北大院理
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藤原 憲秀
北大院理
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河合 英敏
北大院理
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鈴木 孝紀
北大院理
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片桐 康
北大院理
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Susuki Toshihiro
Institute For Fundamental Research Of Organic Chemistry Kyushu University
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鈴木 孝紀
北海道大学大学院理学研究院化学部門
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河合 英敏
北大院理:jstさきがけ
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