Total Synthesis and Absolute Structure Determination of Marine Polyether Macrohdes.

海洋聚醚大分子的全合成和绝对结构测定。

• 批准号: 14580606
• 负责人: FUJIWARA Kenshu
• 金额: $ 2.3万
• 依托单位: Hokkaido University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2002
• 资助国家: 日本
• 起止时间: 2002 至 2003
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14580606/
• 关键词: Marine Natural Products; Polyether Macrolide; Total Synthesis; Stereo-structure Determination; Pectenotoxins; Shellfish Poisoning; Cytotoxicity against Cancer Cells; Polyether Framework

New methodologies for total synthesis and stereochemical assignment of marine polyether macrolides were investigated. In this project, pectenotoxin 2,a diarrhetic shellfish toxin isolated from scallop Patinopecten yessoensis and dinoflagellate Dinophysis fortii, and goniodomin A, an antifungal agent isolated from dinoflagellate Alexandrium hiranoi (Goniodoma pseudogoniaulax), were selected as the synthetic targets. Pectenotoxin 2 was planned to be derived from its 1-epi congener at the final stage of its total synthesis. Full-protected form of the 7-epi-pectenotoxin 2 was successfully synthesized from four segments corresponding to the C1-C7,C8-C20,C21-C30 and C31-C40 parts, through a convergent process including sulfone-coupling, acetal-cyclization, and-ring-closing-olefin-metathesis reactions. Partial synthesis of goniodomin A was planned for the stereochemical assignment. Synthesis of the C1-C7,C6-C16,C15-C25, and C31-C36 fragments were established.

研究了海洋聚醚大环内酯的全合成和立体化学分配的新方法。在该项目中，选择果胶毒素2（一种从扇贝Patinopecten yessoensis和甲藻Dinophys fortii中分离出的腹泻性贝类毒素）和从甲藻亚历山大藻（Goniodoma fakegoniaulax）中分离出的抗真菌剂goniodomin A作为合成目标。果胶毒素 2 计划在其全合成的最后阶段从其 1-epi 同系物衍生而来。通过包括砜偶联、缩醛环化和闭环烯烃复分解反应在内的收敛过程，由对应于C1-C7、C8-C20、C21-C30和C31-C40部分的四个片段成功合成了全保护形式的7-表果胶毒素2。计划部分合成 goniodomin A 进行立体化学分配。建立了 C1-C7、C6-C16、C15-C25 和 C31-C36 片段的合成。

项目成果

K.Fujiwara, Y.Koyama, E.Doi, K.Shimawaki, Y.Ohtaniuchi, A.Takemura, S.-i.Souma, A.Murai: "Syntheses of the D-, E-, F-, and I-Ring Parts of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-D-glucal."Synlett. 2002(9). 1496-1499 (2002)

K.Fujiwara、Y.Koyama、E.Doi、K.Shimawaki、Y.Ohtaniuchi、A.Takemura、S.-i.Souma、A.Murai：“D-、E-、F-和 I 的合成

Kenshu Fujiwara: "Synthesis of the D-,E-,F-, and I-Ring Part of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-D-glucal"Synlett. No.9. 1496-1499 (2002)

Kenshu Fujiwara：“通过从三-O-乙酰基-D-葡萄糖开始的共同策略合成雪卡毒素的 D-、E-、F- 和 I-环部分”Synlett。

Kenshu Fujiwara: "Syntheses of the D-, E-, F-, and I-Ring Parts of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-D-glucal"Synlett. No.9. 1496-1499 (2002)

Kenshu Fujiwara：“通过从三-O-乙酰基-D-葡萄糖开始的通用策略合成雪卡毒素的 D-、E-、F-和 I-环部分”Synlett。

Kenshu Fujiwara: "Total Synthesis of Prelaureatin."Synlett. No.9. 1493-1495 (2002)

Kenshu Fujiwara：“Prelaureatin 的全合成。”Synlett。

K.Fujiwara, S.-i.Souma, H.Mishima, A.Murai: "Total Synthesis of Prelaureatin."Synlett. 2002(9). 1493-1495 (2002)

K.Fujiwara、S.-i.Souma、H.Mishima、A.Murai：“Prelaureatin 的全合成”。Synlett。